


Life's Lessons

by Deangirl93



Series: Life's Lessons Saga [1]
Category: Supernatural
Genre: Age Difference, Alternate Universe - Neighbors, Angst, Anxiety, Dean is 34/35, Dirty Talk, Emotional/Psychological Abuse, Eventual Smut, F/F, F/M, Fluff, Mechanic Dean Winchester, Neglect, Oral Sex, Past Abuse, Past Relationship(s), Reader is 27/28, Rough Sex, Self-Esteem Issues, Sexual Fantasy, Sexual Roleplay, Shameless Smut, Slow Burn, Swearing, Vaginal Sex, mentions of cheating
Language: English
Status: Completed
Published: 2021-01-27
Updated: 2021-01-27
Packaged: 2021-03-12 14:33:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 16
Words: 107,358
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29012115
Author URL: https://archiveofourown.org/users/Deangirl93/pseuds/Deangirl93
Summary: Y/N Y/L/N moves to Lawrence, Kansas to start her life afresh, where she’s hired as the English teacher at the junior high school. Things are going as they would on moving day in a new town, until she meets her neighbor, Dean Winchester. She wasn’t expecting him to be everything she could possibly want. She certainly wasn’t expecting to fall for him, as they get to know each other. He was in a relationship; he had a son, even if he wasn’t actually his. A son who’s in her 8th grade class.Dean and Y/N can’t deny their obvious feelings for each other. Dean knows that he has to break it off with Lisa, but it’s not that easy, having been together for so long. Will he be able to do it before it’s too late and Y/N moves on with her life?(Warnings for individual chapters in notes, as well).
Relationships: Benny Lafitte/Andrea Kormos, Castiel/Meg Masters, Charlie Bradbury/Dorothy Baum, Dean Winchester/Lisa Braeden, Dean Winchester/Reader, Dean Winchester/You, John Winchester/Mary Winchester, Sam Winchester/Eileen Leahy
Series: Life's Lessons Saga [1]
Series URL: https://archiveofourown.org/series/2128341
Comments: 6
Kudos: 25





	1. A Lesson in Settling In

**Author's Note:**

> This series means a lot to me and I hope you all enjoy it! :)
> 
> Warnings: some swearing, first day of work nerves, Dean being cute (yes, that’s a warning lol)

* * *

Y/N leaned against her car, a content smile on her face as she looked up at the house that she was about to call her new home.

The house was clean white, with a grey tiled roof. White wood railings encased the front porch, that had a porch swing in front of one of the windows. The front yard was freshly mowed, with the flower beds on either side of the porch steps. It was a modest, two-bedroom house, with not a whole lot of backyard space, but it was the most rent she could afford with her previous salary. It didn’t matter though; you could make a house a home no matter how big or small it was. Her job as a teacher wasn’t just rewarding when the kids did well, but it was able to put a roof over her head, and that was all she could ask for.

Y/N started with her bags before she opened the large U-Haul trailer attached to her car, and started taking out the boxes. It had been a long journey from Rhinebeck, New York, stopping off overnight in Ohio and then Missouri, but she made it to Lawrence, Kansas that morning, giving her enough time to start unloading her things. Considering it was just her, she knew it was going to take some time, but she was hoping to finish by lunch time so she could explore the town a little.

Luckily for her, complicated things to move like a couch and a bed, weren’t things that she had brought with her. Those things were reminders of what she had done on them with her ex-boyfriend and the last thing she needed in her new house were memories of him. He was the reason she had searched for teaching jobs outside of New York, and luckily, she got the furthest one. She missed her family already, but she needed to get as far away from the memories of him as possible.

Moving her bags and the boxes from the trailer had been the easiest part. It was moving the furniture – dining table and chairs, armchairs, record player, coffee table and two bookshelves – that was going to be the hard task on her own. She started with what she could do on her own, moving all the dining chairs into the house. When she got back to the trailer, she sighed heavily. There were too many things to move.

Y/N stepped into the trailer and started to shift one of the armchairs but growled in frustration as it got stuck on the edge. She couldn’t get the right hold on it to get it off the edge, her legs shaking as she tried to keep it steady.

“Whoa, hey. Let me help you with that” a male voice said behind her. She didn’t turn to see him yet, but watched as he grabbed the other end of the armchair and helped her put it down on the pavement.

“Thanks” she smiled, relieved.

“No problem” he said as he turned to face her.

She almost wished he hadn’t because now her legs were shaking more than they were when she couldn’t hold the damn chair. He was the most beautiful man she had ever seen, handsome but incredibly hot at the same time. The black and white plaid shirt he was wearing was tight across his arms, and she couldn’t help but get lost in his gorgeous green eyes and sinfully pouty lips.

She smiled politely, keeping the thoughts she was having suddenly, at bay. “No, really, thanks so much. I probably would’ve ended up trapped under this chair if you hadn’t stepped in.”

He laughed, laughter lines appearing near his mouth and crinkles around his eyes. “Well, I would’ve hated to see that happen.”

She smiled, not knowing what else to say to him. This was the first time she had ever been this flustered with a man. The sound of his laugh and the way those lines appeared around the creases of his eyes made her heart flutter.

“Can I help you with rest? I mean, I gotta get to work but I can be a little late” he asked, as he looked between the chair and the rest of her stuff.

She looked at the rest of the things and frowned. “You sure? I wouldn’t want to get you in trouble.”

“I’m positive. Helps to be the boss, so…” he smirked, as he shrugged.

She nodded, impressed. “What do you do?”

“I’m a mechanic, I own the auto shop on Main street. Winchester’s. I’m Dean, by the way” he said, as he offered his hand.

She took his hand in hers and tried to ignore the spark she felt radiate through her when their skin touched. “Y/N Y/L/N.”

“Good to meet ya, Y/N” he smiled.

When she smiled in return, Dean was completely floored by her. She was beautiful; dressed in loose boyfriend jeans, a white t-shirt, red converse sneakers and a red bandana around her head with her Y/H/C hair in a messy bun. She really had the girl next door vibe going on. That was dangerous with the situation he was in, so he had to tread lightly. When he saw her from across the street, he was reluctant to help because one look at her, even from a distance and he knew he was in trouble. His mother raised him to be a gentleman though, so he couldn’t hesitate to help a person in need.

With Dean’s help, moving the furniture she did have into the house only took about 20 minutes. She was incredibly thankful for him helping and hoped that it wouldn’t have been too forward to ask if he wanted to grab dinner with her, that night. She straightened out the medium sized, round dining table and chairs with Dean, and sighed in relief once it was done. Her furniture was now in place in all the appropriate rooms. She had to unpack now, which was almost harder than this, but at least she could take her time with it.

Dean looked around her house and nodded, noticing how many boxes had “BOOKS” written on them in black marker. He had only been in this house twice, when the previous owners still lived there before they moved to be closer to their children.

“Big reader?” he gestured towards the boxes.

“Definitely, but I’m a teacher too, so it’s an abundance of books” she laughed, as she looked at them. “It’s a little ridiculous, really.”

Dean laughed quietly to himself, trying to get the teacher fantasies out of his head. She really had to be a teacher.

“Well, I should head out” he said, as he made his way to the door.

She followed behind him and leaned against the doorway. “Thanks for the chivalry.”

“You’re welcome. I guess it’s not dead, after all” he smirked.

She laughed; it felt like the millionth time in the last 20 minutes. He was carefree and had made the tedious process so much easier with his humour.

“I’ll see ya around, Y/N” Dean said, shoving his hands into his pockets as he turned away from her.

“Thanks again” she called out.

Dean walked down the porch steps and turned back. He gave her wink before he walked across the street. She sighed to herself as she watched him walk away, his dark blue jeans doing wonders for his behind, though the black and white plaid was hiding his back from the looseness. She thought against asking him for dinner just yet, at least not on her first day in town. She would give it a couple of weeks, enough time for her to settle into her new job and into the town.

Y/N closed the door and walked back into the main room. Looking at the boxes, she knew it was better to return the trailer to the Lawrence location and then explore the town a little. Get some lunch, do a little grocery shopping. She picked up her bag and keys, heading out of her new house. She would start on the boxes when she got back.

Before she got in the car, she fired off a quick message to her family, telling them she had gotten there safely. It had been text after text and call after call asking if she was okay when she left Rhineback to drive to Lawrence. She reassured her family that all was well, and then drove into town.

* * *

The next day, Y/N was thankful that it was a Saturday. It would give her some more time to set up the house but also start getting ready for the first day of school on Monday. She was nervous about meeting the staff and the students, but she was excited about the new experience. She had walked through town the day before, grabbed the essentials like bedsheets and towels, plus some grocery items for the immediate need. She was already beginning to like Lawrence.

The first thing she did was set up the record player her dad had given to her. Once everything was plugged in where it was supposed to be, she put on one of Creedence Clearwater Revival’s records. She bopped her head along to _Lookin’ Out My Back Door_ as she started to unpack the other records, before starting on the other boxes.

About 15 minutes later, as _I Heard It Through The Grapevine_ played, she stood on the front porch, watching her furniture delivery unload from the truck. Before she even got to Lawrence, she had bought a new bed frame and mattress, couch, office desk and chair online, and thank goodness the place had Saturday delivery. She had made a makeshift bed out her new sheets and pillows last night, and with the way her back clicked and cracked into place when she woke up that morning, she was incredibly fortunate that her new bed was here.

She followed them inside and instructed the delivery guys on where to put the items. As she was helping them, she heard a loud knock on the open door. She turned around and saw a woman, maybe her age or a few years older, standing at the door. Next to her, stood a young boy, probably about 13 years old. Y/N smiled as she walked to the door, seeing a plate of something in the woman’s hands.

“Hi, we saw you moving in and wanted to welcome you. I’m Lisa Braeden, and this is my son, Ben” she introduced themselves, with a bright smile.

Y/N shook her hand and smiled in return. “It’s great to meet you, guys. I’m Y/N Y/L/N.”

“These are for you, I hope you like chocolate chip” Lisa said, handing her the plate of cookies.

“Maybe a little too much” Y/N laughed. “Thanks.”

“Listen, if there’s anything you need, we’re right across the street” Lisa gestured behind her to the house across the street.

Y/N nodded as she looked at the place. It had darker features, but the lawn was equally maintained. “I appreciate that.”

“So, Ben. What grade are you in?” Y/N asked, wanting to engage with Ben a little, who looked quite bored.

“I’m starting 8th on Monday” he mumbled.

Y/N smiled, looking between him and Lisa. “Well, I’m starting work on Monday. Maybe I’ll have you in my English class.”

“Cool.” Ben didn’t seem to care. “Nice choice” he said, gesturing to where the music was coming from before he turned away, walking to the porch stairs and waiting for Lisa.

Lisa looked at him with a “we’ll talk later” look, before she turned to Y/N. “He shouldn’t give you too much trouble, but if he does, you know where I am.”

“I’m sure it’ll be fine” Y/N shook her head.

“Anyway, we should go. Welcome to the neighborhood” Lisa said, smiling again.

“Thanks” Y/N smiled.

She watched as Lisa and Ben walked across the street, clearly waiting to be behind closed doors before she talked to him about what just happened. Hopefully she wasn’t too harsh on him; no kid would want to meet their new teacher outside of a school setting. Y/N walked inside the house and saw that the delivery guys were done. She signed off on the delivery and the guys left. She picked up one of the boxes still in her living room and walked to the second bedroom she was using as an office. She was excited to set it up and get started on some work for Monday.

* * *

Y/N sat in her car in the parking lot of the school. She had gotten there a little early, just trying to calm herself down before going in to meet the principal. She had spoken to him for her phone interview and again when she got the job, so she was familiar with him. He seemed like a nice man and she just hoped that the rest of the staff were the same way. She was more nervous about the students. Moving schools wasn’t just hard as a kid.

She checked her make-up in the mirror and then got out of the car, walking towards the entrance. She fixed her white top and smoothed down her brown skirt, thankful that she had chosen brown sandals with a small heel instead of something higher. She didn’t need anything to go wrong today. Once inside, she walked over to the administration office, as guided by the signs. At the very first desk, sat a red-headed woman, the name plate on her desk reading: **Anna Milton – Receptionist**.

When Y/N approached her desk, she looked up from her computer and smiled.

“Hello, how can I help you?” she asked.

“Uh, hi, I’m Y/N Y/L/N. I’m starting here today and need to meet Mr. Shurley first” Y/N replied, trying her best to keep her nerves at bay.

“Oh of course” she picked up the phone and pressed a number.

Y/N waited a minute or so before a short man with greying hair and a beard, walked out of an office at the back of the room. He saw her and smiled, extending his hand as he approached her.

“Miss Y/L/N, wonderful to meet you” he said, shaking her hand.

“You too, Mr. Shurley” she smiled, as confidently as she could.

“Alright, let me show you around before your first class” he walked ahead of her, not leaving her too far behind.

It took Chuck, as he insisted on being called by his first name when it was a one-on-one basis, a few minutes to show her around the main parts of the school; the staff room, the library, the gym and the cafeteria. After that, he took her to the classroom she’d be using, just before the students came in. They watched as they came in, sitting down at their desks. Ben walked in and she smiled at him, but just received a little twitch of his face back. They all looked scared to see the principal in the room.

“Class, I’d like you meet Miss Y/L/N. Your new English teacher. So, make her feel welcome” he said to them in a commanding voice, before he turned to her. “If any of them give you any trouble, just send them down to my office.”

“I’m sure I won’t need to” Y/N looked between him and the students.

“Alright, take it away” he smiled before he left the room.

As soon as he was gone, the class erupted into loud voices as they began chatting away. Y/N sat on the edge of her desk, her legs and arms crossed as she waited, patiently. She would give them a few seconds before she got their attention. Before she could do that however, Ben looked at her and then at the rest of his classmates.

“Guys” he called out. The noise level didn’t go down.

“Last one to be quiet has to tell their next teacher why they were late” she called out.

The noise level dropped instantly.

Y/N smiled, happy that worked. “Alright. As Mr. Shurley said, I’m Miss Y/L/N. We’re going to start off with the role. As I call out your names, you’re going to tell me what you read over the summer and a short answer about what you liked or didn’t like about it.”

For majority of the class, things went well. Most of the students were well behaved except for one group of three boys who kept talking and disrupting the others around them. They were rude and weren’t listening to her when she asked them to stop several times. She would have to keep an eye on them. To say that her first lesson had been difficult would be an understatement, but she got through it. That’s what mattered.

Y/N had a break in which prepared for her class with the 7th graders. They were a breath of fresh air and exactly what she needed after the previous class. They were much more engaged and a lot softer spoken, so while she would have to get them out of their shells a little bit, they were pretty well behaved.

At lunch, Chuck introduced her to a few more of the teachers. She shook hands with everyone and engaged in conversation. The usual chatter about where she was from and how she got into teaching. As she sat down to eat, she looked over some of her messages. She smiled as she saw one from her sister, sending off a quick reply to tell her she was doing okay.

“Mind if I join you?” a voice asked.

She looked up to see a man with brown short hair and blue eyes smiling at her. He was adorable, looking cute in his white shirt with rolled sleeves, black pants and blue tie to match his eyes.

She smiled in return and nodded. “Sure, of course.”

He sat down across from her with his lunch. “I’m Castiel Novak, history teacher. Everyone calls me Cas, though.”

He offered up his hand and she shook it. “It’s great to meet you.”

Just as he was about to say something, a red-headed woman, not Anna, walked over. “Hey, you must be the new English teacher, I’m Charlie.”

“I’m Y/N” she said, shaking her hand.

“Charlie teaches Math but she’s a computer whiz too. Helps out the I.T. guys every now and then” Cas told her as Charlie settled into the seat next to him.

Y/N smiled approvingly. “Wow, that’s amazing.”

“Thanks. They ask me because I think they secretly know I’m better at it than them. I was in the corporate line for a while, but then I moved back home to help my mom” Charlie explained, between bites of her salad.

Y/N liked her already, her nerdy vibe with colourful plaid shirt and band t-shirt suiting her chirpy personality. Cas was a little quiet, but there was a calm presence to him. Though she had no doubt he had the ability to get kids to listen to him straight away.

“Yeah, we’re all glad she came back and stuck around” Cas smiled at her.

When she smiled in return, Y/N had to ask. “So, you two…?”

They both laughed as they looked at each other and then back at Y/N.

“No, we’ve just been friends for a really long time. I have a girlfriend, Meg. She’s a nurse at Lawrence General. She’s tougher than nails and I don’t know how I got her” Cas replied, laughing slightly.

“Yeah, and I’ve just started dating a few weeks ago. Her name’s Dorothy and she’s a writer for the Kansas City Times. She’s really cool” Charlie smiled softly.

Y/N nodded, understanding. “They both sound amazing. I can’t wait to meet them some time.”

They continued talking over lunch and Y/N couldn’t have been happier to have met them. They were both incredibly kind and lovely people, and she was really starting to get along with them.

As lunch finished and they went their separate ways, Y/N smiled as she walked to her next class.

Hopefully moving to Lawrence, Kansas was going to be the best decision she’d ever made.


	2. A Lesson in Fitting In

**Summary for the Chapter:**

> Y/N has survived her first week in a new town. However, after discovering that Dean and Lisa are in fact a couple, she wants nothing more than to lock herself up in her house. The neighborhood Saturday barbecue comes around, and Y/N finds herself by his side when Lisa isn’t around. Their conversation brings up some thoughts for her about Dean and Lisa’s so-called ‘perfect’ relationship.

**Notes for the Chapter:**

> Warnings: swearing, slight angst, reader misses her family, mentions of past family struggles, mentions of reader’s ex.

* * *

Y/N’s first week didn’t go as great as she expected.

She naively thought things would be good after the first day, which had started a little wonky but ended up being better once she met Cas and Charlie. She had become really friendly with them, and she was glad that they were a highlight of each day. Her 7th graders were great, but she had to do a lot of work with them to make them come out of their shells. Her 8th graders on the other hand… she just didn’t understand how to get through to them. Some of them were loud and disruptive, a couple of them were bullying another girl, and others just didn’t seem to care at all. Ben was a good kid, but he got easily swayed by the loud ones. They had so much potential, and they had to start being better if they were ever going to survive high school.

She walked out of the grocery store, pushing a shopping cart with two heavy brown bags. After finishing up at school, she decided to go and buy a few essentials plus some stuff to make dinner. She was looking forward to a nice meal she cooked and a glass of wine, maybe two. As she drove through town to get home, she smiled. Despite everything, Lawrence was a peaceful town. She had to hope that she could strap in and really get through to the kids, so that living here would be worth it.

As she drove down her street, she smiled as she saw Dean sitting on his porch steps. She pulled into her driveway and got out of the car, smiling as she saw him talking on the phone. She walked over to her trunk and opened it, picking up the two bags in there. She left the trunk open, as she struggled to hold the bags, cursing the guy at the check-out for filling them so much to save on bags. Suddenly, there was a pressure on one of the bags, as it ripped at the bottom, not being able to handle the weight of the items. Two cans fell and started rolling down her driveway.

“Shit!” she yelled, as she manoeuvred the bags and tried to hold them both in one arm.

Dean, who was still on the phone as he sat on the porch steps, saw everything from across the street.

“Sammy, let me call you back” He quickly hung up the phone and rushed across the street. He got to the end of the driveway just in time and swept up the rolling cans. Y/N saw him and beamed, relieved.

“Thank you” she breathed heavily.

“No problem, can’t have run away cans on the street” he smiled, as he continued to hold them. “Here, let me get that for ya.”

He picked up the broken bag from her arm and held it, his hand at the bottom.

“Between my furniture and my groceries, I think you’re my savior” she laughed.

Dean shook his head, a smirk on his face. “I take the job very seriously.”

“I hope that call wasn’t important?” she asked, knowing he had been on the phone with someone.

“Nah, just my pain in the ass little brother. It’s okay, he’ll get over it” he replied, laughing slightly.

Y/N laughed with him, getting lost in his green eyes again. He looked even more sexy and handsome today, now wearing a red and black plaid shirt on top of a black t-shirt and dark blue jeans. She had told herself she’d wait to ask him for dinner, and now she couldn’t think of a more perfect time, having just saved the items for dinner.

“Hey, um… are you doing anything tonight? I was going to make dinner for myself but if you’re free-” she started to ask but got cut off by a voice coming from his house.

“Dean!” a female voice called as she came out onto his porch.

Y/N’s heart sunk as Ben’s mother, Lisa, came out and looked around. When she spotted him, she waved him in.

“Can you help with dinner?” she asked and then walked back inside the house. Y/N had never seen which house Lisa and Ben had come from that day, so this was shocking. The guy she was kind of crushing on was Lisa’s boyfriend. Ben’s dad. Fucking great.

“Sorry, I didn’t realize-” Y/N started but Dean shook his head.

“It’s okay, Y/N. I should go” he helped her take the bags inside the house and then awkwardly stood there.

“I’ll see ya around” he gave her a quick nod before he rushed off, before she could say anything.

Y/N frowned as she closed the door behind him. She leaned her head against it as she groaned. Why did she have to start liking him without knowing his situation? She moved away from the door and walked into the kitchen. She was going to get started on dinner for one and try to stop thinking about her ridiculously good-looking neighbor.

Dean walked into his house, finding Lisa in the kitchen. She had a blank expression on her face, as she chopped up the vegetables.

“What do you need?” he asked.

“Why were you talking to Y/N?” she asked in return, abruptly.

Dean blinked a few times, confused by her question. “She was just struggling with some broken grocery bags. I helped her.”

“Whatever” she mumbled, as she moved away to the stove.

Dean shook his head, walking out of the kitchen and to the backyard. Lisa was suddenly in one of her moods and he needed to get away. He usually hid out in the garage until things cooled down with her.

* * *

Y/N was thankful to have finished her first week and now move into another Saturday. She still had a few boxes that needed to be emptied, having done most of them last week and then sporadically through the week. She was going to do that in the morning and then look over her plans for the next week of school, before chilling that night and having a drink.

After a quick breakfast and putting on one of her phone playlists this time, she got started as her favorite Kaleo song came through the speakers. She smiled sadly as she put up some of the pictures she hadn’t yet, her heart aching knowing she had left her family behind. One of her with her sister and parents. One of her sister and brother-in-law with her nieces; the younger one having just been born before Y/N had to leave. One of just her and her sister. This was the one thing that made her regret leaving: her family. She stepped back as she looked at the photos on the mantel above the fireplace, remembering all the wonderful times she had with her loved ones.

The doorbell rang, interrupting her thoughts. As she walked to the door, Y/N looked up at the clock, seeing it was 12.30pm already. She opened the door, her smile becoming a bit forced once she saw it was Emily Charlton, one of her middle-aged divorced neighbors. She had already been over several times that week with baked goods, which she ended up feeding to the birds after one bite.

“Hi, Emily. What can I do for you?” she asked, politely and hoping the woman would leave soon.

“I’m just here to find out if you got the fliers in your mail about the barbecue today” she replied, her big white teeth beaming.

“Oh, yeah, I did see that” Y/N said, remembering the two fliers she had received.

“Well, it’s at Sid and Olivia’s and starts at 1, and it would be good for everyone to meet you” Emily continued to smile. She pointed at the house, then primped her blonde hair with her long acrylic nails.

Y/N rolled her eyes while she wasn’t looking. “I’m sorry, Emily, I can’t. I just have a lot of work to do-” she started but Emily waved a finger, her fake nails looking like they could gauge an eye out.

“Nonsense, I absolutely insist on you coming to lunch. There’s still so many on the street you haven’t met yet” she insisted.

Y/N sighed, shaking her head. It was better to give in than keep arguing. “Sure.”

Emily laughed in a high pitch tone, making Y/N cringe. “Wonderful!”

“Great” she mumbled, under her breath.

“So, we’ll see you soon, and uh” Emily looked her up and down, causing Y/N to frown. She looked down at herself, dressed in just a loose, plain red t-shirt and her boyfriend jeans. Emily smiled one more time, fake as ever, before she strutted off.

Y/N closed the door, wanting to shut everyone and everything out, but she wasn’t going to do that. She was going to glam herself up and go to the barbecue, to rub it in Emily Charlton’s face that she could be fake all she wanted, it wasn’t going to affect her.

She frowned as she thought about how she shouldn’t go there empty-handed. If she did, she’d probably be the talk of the street and be highly judged for it. She normally didn’t care what people thought of her, but in this case, if she could avoid it, she would. It was better to be slightly late. Plus, who showed up right on time, anyway? She quickly searched around in her kitchen cupboards and found a box of Betty Crocker brownies in her pantry. She quickly made the pre-mix. She smiled. She was good, even in a time crunch. No one needed to know they were from a box. She put the brownies into the oven and set the timer.

Y/N showered and washed her hair, drying it into a natural, summer-y look once she got out. She got dressed into a red, cap sleeve summer dress, with a small white flower print on it. Looking at the clock, she saw that it was 1pm.

When the timer went off, she walked back into the kitchen and took out the brownies, waiting for them to cool. She went back into her room and applied her make-up, keeping it simple with a little foundation, some mascara and a little lip gloss. She put on her wedge heels and her small bag across her body. After a few minutes when she was dressed and ready, she cut the brownies and put them in a container. She put her sunglasses on, before walking out of the house. She locked up and put her keys in her bag, climbing down her porch stairs before walking down the street.

Y/N was nervous to be around so many people, hearing the sounds of music and laughter coming from Sid’s house. Especially if most of those people turned out to be like Emily Charlton, but she couldn’t let them scare her if they were. She wouldn’t let anyone overwhelm her and push her around again. She had suffered enough the first time, and she wouldn’t let it happen again.

She saw some people walk in through the side entrance to the backyard, as some older teens played touch football in the front yard. Y/N followed behind those people, looking out for Sid or Olivia. She looked around the large backyard as Nathaniel Rateliff crooned away from the large speaker on the back porch. She had seen them around, Emily telling her who they were, so Y/N hoped she could spot them properly and didn’t confuse them for someone else. Luckily, she heard Emily’s high pitched “Olivia!” and saw her hugging another blonde woman.

Y/N walked over, putting her sunglasses on her head. She smiled as she approached Olivia, laughing to herself as her face looked just as uncomfortable to be around Emily.

“Olivia, hi. I’m Y/N” she said, smiling.

“Oh yes, so good to finally meet you” Olivia smiled, shaking her hand. “Emily told me about you, welcome to the neighborhood.”

“Hello again, Y/N” Emily’s fake smile beaming once again.

“Hi” Y/N nodded at her before turning back to Olivia. “I thought I’d bring a little something.”

She handed over the container.

“Oh, you didn’t have to, but thank you. Okay, Sid’s handling the grill and there’s already plenty, so please help yourself. Can I get you a beer? Wine? Something stronger to deal with Emily?” Olivia laughed, when Emily had walked off to speak to someone else.

Y/N’s eyes widened with surprise, as she laughed too. She liked Olivia already.

“A beer would be great” she continued to laugh.

Olivia bent down and took a beer out of an ice bucket. She opened the lid with a bottle opener and handed it to her.

“So, what do you do, Y/N?” Olivia asked, as she sipped her wine. She started walking towards the food table and Y/N followed beside her.

“I’m an English teacher, junior high” Y/N replied, before taking a sip of her beer.

Olivia stopped and smiled at her, a fondness in her eyes, which Y/N would’ve found strange but something about her look was pleasant.

“My mom was an English teacher. She passed last year, but it still feels like yesterday” Olivia quietly told her.

“I’m sorry, Olivia” Y/N gave her a sad smile. “She must’ve been amazing, if she was anything like her daughter.”

Olivia beamed; her eyes slightly watery. She wrapped an arm around Y/N’s shoulders as they walked towards the food table.

Y/N’s smile dropped when she saw who was standing at the table. Lisa was shifting things around, making place for everything on the table. Dean, who was dressed in jeans and black half-sleeve button-up shirt, came up behind her. She turned her head and kissed him on the cheek. Y/N felt a tightness in her chest but chose to ignore it. Olivia walked over to the table and placed her container down, making some small talk with Lisa. Dean turned his head, smiling when he saw Y/N.

Dean could feel his heart racing. She was stunning, every single thing about her. From her hair, to the way she looked in that summer dress, which had a slit on the side, giving a peek of her smooth leg. He couldn’t be looking at her, not with Lisa standing right next to him. Y/N smiled in return, getting lost in his features yet again. He was so incredibly good-looking, it hurt to look at him.

Y/N looked away from him when Olivia tapped her shoulder. She smiled at her, trying not to let it show that she and Dean had been staring at each other.

“Aren’t they perfect together?” Olivia said, not really seeking a reply as she smiled at Dean and Lisa.

“Yeah.” Y/N smile faltered.

“So, help yourself. I’m just going to check in with Sid and see if he needs anything. I’ll be back” Olivia walked off, leaving her to go to her husband.

Y/N walked closer to the table, trying to smile when Lisa noticed her.

“Hi, good to see you” Lisa smiled. “Can I get you anything?”

Y/N shook her head. “No, I’ll help myself, thanks.”

“Okay” Lisa turned from her to Dean. “I’m just going to check where Ben is, can you plate some for me?” she leaned in and kissed his cheek.

“Sure” he nodded, before grabbing a plate and putting food on it.

Y/N smiled as Lisa walked past her and then looked over at Dean. She didn’t know for sure, but it felt like Lisa was being a bit aloof with her. She chose to ignore it for now. She walked closer to the table, and Dean looked up at her.

“It’s really good to see you” he said. The way he was looking at her was different to how he had been looking at Lisa.

She felt her cheeks get a little hot. “It’s good to see you, too.” Y/N started to put some food on her plate.

“So, how-” he started but was cut off by a shrill voice calling out her name.

“Y/N! Get over here, young lady!” Emily yelled from across the yard. She had a gaggle of middle-aged women around her.

She turned back to Dean; her eyes wide. “Is there any way I can get out of going there?”

Dean laughed. “Afraid not.”

She groaned, as she closed her eyes. “Wish me luck.”

“You don’t need it” Dean smirked.

Y/N opened her eyes, smiling when she saw him smirking at her.

“You can handle a few divorcee’s and housewives” he assured her.

She bit her lip, as she shook her head. Somehow, he had managed to ease her mind. “Thanks.”

Y/N took her plate and beer, throwing her shoulders back and walking over there with confidence. Dean admired her as she walked away, checking her out as her hips swayed. It was dangerous to be doing that with so many people around, but he took his chance. He picked up two plates and walked away from the table, in search of Lisa.

* * *

Y/N couldn’t hide the boredom on her face, as the divorcee’s and housewives asked her questions about her life.

“So, Y/N, are you seeing anyone special?” one woman asked.

“Nope” Y/N answered around a mouthful of hot dog, not really caring about anything other than food at that point.

“Why not? A pretty, young girl like you” equally nosey Jill, added.

Y/N shrugged, still eating. “I just got here and want to take my time, you know?”

Emily shook her head. “No, there’s definitely more to the story. It was a bad break up, wasn’t it? That’s why you moved here.”

Y/N frowned, glaring at Emily. “You know, it’s really not something I want to talk about.”

“Oh, Y/N, if you don’t talk to us, who can you talk to? We’re here to help” Emily gave her the best sympathetic face she could probably muster.

“You know what? You could help me with this” Y/N handed Emily the empty plate. “I’m going to get another beer.”

She didn’t stick around to see the shock on Emily’s face to her abrupt departure and Y/N’s plate in her hand.

Y/N felt the anger simmering in her belly as she walked away. The last thing she needed was advice from that woman. She just wanted to grab a beer and go sit somewhere in the front yard, away from everyone else. She picked up a bottle and opened it, taking a sip as she walked away. She walked out to the front yard and looked around. There was a large tree with good shade near the fence, which would be nice and secluded. As she walked closer, she noticed someone leaning against it. She walked around, smiling when she saw Dean with a beer in his hands.

“Mind if I join you?” she asked.

“‘Course not” he smirked, as he shifted over.

“I seriously had to get away from those women” Y/N groaned, sitting down on the ground next to him.

“Yeah, they’ll do that to ya” he laughed, sipping his beer.

“Well, I handled it like you said” she smiled, holding her bottle towards him.

He nodded, approvingly, clinking his bottle to hers. “Nice.”

A comfortable silence fell between them, as Fleetwood Mac could be heard from the backyard. Y/N looked at him, appreciating his features now that she was closer. Freckles scattered under his eyes and on his nose, and his eyes were even more striking up close.

“So…” she trailed off, thinking of what to ask him. “Did you grow up here?”

He nodded, a small smile appearing on his face. “Yeah, born and raised. My parents are still in the same house we grew up in. My little brother lives in Kansas City with his wife.”

“Are you and your brother close?” she asked.

“Yeah, it’s always been me and Sammy. I mean, don’t get me wrong, my parents were good with us, but there were times when they’d fight, and I’d have to look out for him” he replied, looking down at his bottle.

Y/N frowned, and Dean noticed. “Oh, don’t worry, my parents were great, it’s just sometimes… they didn’t see eye to eye, you know? They’re good now, though. Have been for a long time.”

She smiled, seeing how fondly he spoke of his family. They must’ve been close. She was missing hers a lot.

“What about you?” he asked in return.

“I was born and raised in Rhinebeck, New York. No brother, but sister instead. She’s married to a great guy, so he definitely feels like a brother” she told him, a sad smile on her face. “They have two beautiful daughters, one was just born before I left so I’m going to miss seeing her.”

“Wow. From New York to Kansas” he muttered, laughing. She joined in. “Why the big move?” he wondered, as he took another sip of his beer.

“I…” she breathed out, shaking her head. “I needed to get away. It just became… too much.”

Dean nodded, but he understood that that wasn’t the whole story.

“But this is a great town, not too different from back home, so that’s a plus” she said, smiling at him.

Dean smiled in return. “That’s great.”

They looked into each other eyes, and she felt that familiar fluttering in her stomach.

_Don't, don't break the spell  
It would be different and you know it will  
You, you make loving fun  
And I don't have to tell you but you're the only one_

The words of the song were beginning to freak her out as they maintained eye contact. Y/N quickly looked away. This was unsafe ground they were about to tread.

“How’d you meet Lisa?” she asked, quickly changing the subject.

Dean breathed deep, with a long exhale. “She was here from Indiana visiting some friends, and we met one night at a bar. It was a one-time thing, but then a few months later she moved here with Ben when she got a job opportunity. We met up again… and we’ve been together three years.”

“Wait…” she thought about everything he just said, suddenly confused. “Ben’s-”

“Yeah, he’s… not mine, technically. It feels like he is, though” Dean finished for her.

“Gosh, I really should’ve guessed with the last names” she shook her head, rolling her eyes at herself for not realizing sooner.

“It’s all good, Y/N” he chuckled.

“Well, you guys look really close” she said, trying to sound happy.

“Yeah” he huffed, knowing he and Lisa were far from close these days.

Maybe coming to talk to him hadn’t been such a good idea. She seriously had to start liking a taken guy, didn’t she? At least he wasn’t married. _Oh yeah, Y/N. That makes it better_ she thought, as she closed her eyes at her own stupid thoughts. Though she had to wonder, if things were great between him and Lisa then why was he sitting out here, far away from her?

Dean looked up at her and looked into Y/E/C eyes again. Sitting there and talking to her about Lisa just didn’t feel natural. It really did feel like he was living a lie, it had felt like that since way before Y/N showed up.

Y/N quickly looked away from him. She needed to leave. She quickly stood up, dusting her dress off.

“I should really get going. I have a lot of work to do” she said, turning to him as he stood up.

“On a Saturday?” he asked, confused. Dean took the empty beer bottle out of her hand. The brush of his fingers against hers sent a tingling sensation through her arm and over her body.

“Life of a teacher” she quickly joked, pulling her hand away.

Dean huffed a laugh, scratching the back of his neck. “So, I’ll see you around?”

She nodded, a small smile on her face. “Yeah.”

Dean looked back at the back yard, before looking at her. “I better find Lisa.”

“Thanks for the chat” she said, playing nervously with the strap of her bag.

“No problem” he smirked.

He slowly walked backwards and gave her a small wave, before turning and walking away.

Y/N watched him walk to the back yard before she turned and walked down the sidewalk. She quickly made it home, closing the door behind her. She walked into her bedroom, dropping her bag on the chair and then stripped off her dress and shoes. She changed into her large sleep shirt, which came down to just above her knees. She threw her hair up in a bun and walked into her bathroom, taking the make-up wipes to rub off her make-up. She washed her face and wiped it down with a small towel, flicking the light off as she left.

As she went about that routine, her mind was on Dean. Just a short amount of time to talk, a few looks between them, a small touch of his hand against hers, and she couldn’t stop thinking about him. There was an air about him, almost like you could trust him completely. He would take care of you and never let anything happen to you. There was a sadness behind his smile, however, and she could feel that it had something to do with life at home. He and Lisa weren’t the perfect couple they wanted people to see them as.

She walked out into the living room, her phone in hand. She dropped down on the couch, tucking her legs up. She scrolled through her phone, finding the name of her best friend, Katie, and sending her a quick text to see if she could talk. They had been best friends since college, and right now, she needed to talk to her about Dean. Maybe she could give her some advice on how to stop the way she was feeling. When she got a text back saying she could talk, Y/N called her.

“Hey, sweetie” Katie greeted.

Y/N smiled, closing her eyes. “You have no idea how good it is to hear your voice.”

“It’s good to hear yours too. Though… you do sound a bit… off” her friend’s concern was evident in her voice.

Y/N scoffed and thought about what to say. “Well, it’s been a week in a new town… and I already have a guy problem.”

“Wow, that was quick” Katie commented.

“Yeah, well…” Y/N trailed off, playing with the edge of her shirt on her knee. “I wasn’t expecting for it to happen so fast, either. Especially after Ethan.”

“Okay, what’s his name?” Katie asked.

“Dean” a smile grew on Y/N face’s as she said his name, but it quickly dropped. “But before you say anything, he’s with someone and she’s got a kid, who’s practically a son to him.”

Katie let out a whistle. “Wow.”

“Yeah” Y/N agreed.

A silence fell between them, and Y/N knew that Katie was thinking.

“Well, as much as you probably don’t want to hear it, I think you got to let this one go” she said, finally.

Y/N sighed. “You’re right. I was already thinking it. I guess I just needed someone else to say to me, so I didn’t do anything stupid.”

“You’re a far more rational person than I am, so I doubt you would’ve” Katie reassured her.

Y/N huffed, rolling her eyes. “You haven’t seen what he looks like.”

“Well, photos when and if you get the chance” Katie laughed.

Y/N laughed, shaking her head.

They spent another half hour catching up on everything back home. It made Y/N miss everything even more, but she was glad to get the latest news. After they ended their chat, she got up from the couch when she noticed what the time was. She started fixing herself something for dinner, when she heard voices from across the street. She looked out the window, seeing people going home from Sid and Olivia’s.

Y/N watched Dean, Lisa and Ben walk back to their house. Dean and Lisa were holding hands, as Ben walked in front of them. Y/N felt her heart sink, seeing them look like a happy couple. Though it seemed that things weren’t all that great, or at least that was the impression she got from the way Dean looked at her.

Y/N shook her head and went back to making dinner. Once she was done, she settled in on the couch with her plate, a glass of wine and FRIENDS on Netflix.

It was silly of her to think that anything would ever happen with Dean. Even if he wasn’t with Lisa, she had only been around Dean twice. That wasn’t enough time to start thinking of him. This was just a crush, and it would go away soon.

Or so she hoped.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	3. A Lesson in Faking It

**Summary for the Chapter:**

> Monday morning is off to a bad start as Y/N’s car refuses to start, but she receives some help from Dean. As an IOU when he refuses to let her pay full price for the car service, Y/N invites him dinner. Realizing what it could imply, she backtracks and invites Lisa, too.

**Notes for the Chapter:**

> Warnings: Swearing, some angst, Lisa being aloof, social insecurities, alcohol consumption to deal with nerves.

* * *

Monday arrived too quickly for Y/N to be happy about it.

She had managed to get some revisions done on her lesson plans, so she was prepared for her classes in terms of content. She just hoped for the strength to deal with the kids this week. She really hoped this week would be better than her first.

She woke up as soon as her alarm went off and started getting ready. After her shower, she dried her hair and got dressed into a purple A-line dress, with a collared neckline. She wore her black, pointed toe shoes, that had a short heel, the most sensible heels for school. After applying a little bit of make-up, she fixed her hair and pinned it into a bun. Seeing that she had some time before she left, she made herself a quick breakfast, of yoghurt and fruit and a piece of toast with peanut butter.

Breakfast was a lot different at the Winchester/Braeden household.

Dean was at the stove, working on scrambling eggs. Ben placed plates on the kitchen counter, the bacon already crispy and done, on the counter already. As Dean turned to put the eggs on the counter, he lifted his arms up, as Lisa ducked underneath to get past him. She took out one ceramic mug and a travel mug, filling them both with coffee.

“I’ve got soccer try-outs after school, so I won’t be done until 5” Ben said, pouring himself some orange juice.

“I’ve got a meeting today and it might run late, so can you get him?” Lisa asked, putting Dean’s travel mug in front of him.

Dean took out some eggs on Ben’s plate. “Yeah, I’ll come get ya.”

“Thanks” she mumbled, fixing her own plate of breakfast.

Dean ignored her lacklustre response, as he practically shovelled food into his mouth. He was going to be late if they didn’t leave now.

“And then drop me off at my science partner’s house. We’re working on a project together” Ben explained.

“Sure” Dean nodded, as he ate.

“They’re going to bring you back home, right?” Lisa asked.

Ben nodded but continued eating.

Dean looked between them, practically inhaling breakfast. “Alright” he mumbled around the last bite of food in his mouth. “You ready?”

“Yeah” Ben replied, gulping his juice down.

Dean put his plate in the sink, followed by Ben’s as he grabbed his coffee. “Bye.” He leaned over and kissed Lisa’s head, a habit that he hadn’t dropped even if it didn’t mean what it used to, before walking to the door.

“Bye mom!” Ben called out.

“Have a great day!” she called back before Dean closed the door.

* * *

“Fucking start, you piece of shit!” Y/N yelled, as she turned the key to her car in the ignition. All she got back was a grinding sound, and nothing else. It would stutter and die down but pick up again every time she turned the key.

“Damn it!” she slammed her hands on the wheel as she sat back, shaking her head.

This is what she got for driving all the way to Kansas in this piece of crap car, which might as well have been held together by duct tape and dental floss. She got out of the car with her phone, trying to look up a number for a mechanic.

Dean walked over to the Impala and was about to get in when he heard an awful sound coming from across the street. He looked up to see Y/N’s car still in her driveway, which was the source of the noise. He watched as she got out, a frustrated look on her face.

“Hey” he called out.

Y/N looked up, smiling tentatively. That’s not really the mechanic she wanted. Well she did, but she shouldn’t.

“Get in the car” he said to Ben, as he walked across the street to her.

“That doesn’t sound good” he told her as he reached her.

She shook her head, as she frowned. “Yeah, I’m going to be epically late by the time someone shows up.”

“Okay, there’s no freaking way you’re calling someone else, I’ll give you a ride to school and tow this to the shop later” he explained.

“What?” she asked, shocked that he offered without hesitation. “No, Dean, it’s really okay-”

“No, no, you’re not talking me out of this. I’m taking Ben to school; it just makes sense” he gave her a pointed look, letting her know he wasn’t backing down.

“Dean, I really can’t. With Ben… it’ll be really awkward, I’m his teacher” she protested.

“Look, I’ll drop you guys off around back, no one’s gonna see you. Okay?” he insisted.

She was going to be late if she didn’t take the offer.

“Okay” she sighed, defeated but relieved. “Thanks.”

Dean smirked. “No problem, sweetheart. Come on.”

They walked over to the Impala and Y/N admired it as they got closer. She had obviously seen it a few times from across the street, but she was excited to take a ride in it. She loved the look of classic cars because of her dad, and she felt a heaviness in her heart as she thought about him, so far away back home.

“She’s beautiful” she said, as she ran her hand over the smooth finish. The sleek black shone in the sun, showing her that Dean loved his car immensely.

“Yeah, she is” he agreed, grinning.

Ben smiled at her nervously as she got into the car. Y/N just smiled, feeling slightly awkward that she was in a car with one of her students, and his surrogate dad. She just had to avoid conversation about school and hopefully everything would be okay.

They were on the main road to school pretty quickly, the silence in the car too much for Dean to bear. He leaned forward and switched on the music player, his Zeppelin tape coming to life through the speakers. Y/N smiled and bopped her head along to _Out on The Tiles_. Dean looked at her from the corner of his eye and smirked at her reaction to his music. Lisa didn’t really like listening to his music.

“I’m gonna go back and get your car later” he said, lowering the music slightly. “I’ll take a look at it.”

“I really can’t thank you enough, Dean” she smiled.

“Hey, it’s my job” he shrugged, as he looked out at the road. “Swing by the shop after work and we can sort everything else out.”

“Sounds good” she nodded.

Another silence fell between them, the music the only thing they heard but the lyrics to the song caused an air of awkwardness to fill the car.

_All I need from you is all your love_   
_All you got to give to me is all your love_   
_All I need from you is all your love_   
_All you got to give to me is all your love_   
_Oh yeah, oh yeah_   
_Oh yeah, oh yeah_

“So…” Dean trailed off, trying to find something to say. “You uh… you into Zeppelin?”

“Yeah!” she exclaimed. “Grew up on this and pretty much all classic rock, thanks to my dad. I got all his records and his record player when I moved out here. Said he wanted me to take a piece of home with me.”

Dean let out a whistle as he glanced at her. “That’s awesome.”

“Yeah” she sighed, looking out the window.  
“I started listening to this stuff because of my dad, too” he told her. “Hell, I got a lot from him, the car too.”

“Really?” she asked, surprised. “Your dad gave up a mint condition Impala?”

Dean raised his eyebrows as he looked at her. “You know this is an Impala?”

“Yeah” she shrugged like it was no big deal. “I went to a car show once with dad. I saw one there and knew it was the same once I saw yours.”

Dean, however, thought it was a very big deal. _Damn it, just one more thing to like about her_ he shook his head, getting rid of other things he was thinking of.

“Well… it’s still in the family, so it wasn’t much of a sacrifice” he laughed.

“Still… he must really love you to just give it you” she said, turning to him.

Dean looked at her and saw the small smile on her face. As he thought about it, he knew that she was right. He and his dad had their issues sometimes, but there’s nothing they wouldn’t do for each other. He smiled back at her and then looked at the road. He knew he had to get this conversation back to the safe zone before they arrived at school.

“So, you’re into cars?” he asked, casually.

She laughed, shaking her head. “Only for the look of them. I have no idea about them otherwise.”

Dean shook his head, with a smile on his face. She had a great laugh and he suddenly felt the need to hear it as much as he could.

“Ben’s into cars and this music too. Right, Ben?” he asked the kid sitting in the backseat.

“Yeah” Ben mumbled.

“Lisa not so much though” Dean mentioned, but he realized that he only did that so that it didn’t seem like he had forgotten her about for a second. It scared him how drawn he was to Y/N.

A few moments later, Dean pulled up at the back of the school. They could see the main drop-off area from there, as kids yelled goodbyes to their parents and hurried in.

Dean looked up at the rear-view mirror, seeing Ben gather his things. “See you at 5, kid.”

“Yeah. Bye Dean” he mumbled, as he opened the door and shut it, the hinges squeaking.

Dean watched Ben walk towards the entrance, then turned to Y/N.

“Thanks for the ride, Dean” she said, gathering her bags. She handed her car keys to him, for later.

“No problem” he smirked, as he leaned back, one arm outstretched, his wrist leaning on the steering wheel.

Y/N tried not to sigh noticeably, as she was flustered at the sight of him. Did he know what he was doing to her? He had to know, right?

“I should go” she laughed, trying to hide her nervousness.

“Wait” he said, as he pulled out his phone. “Put your number in and I’ll text you when I’ve picked up your car.”

“Sure” she said, quietly.

She was a little nervous about him having her number. Would Lisa think something of it? It was just two people exchanging numbers, that’s all. Plus, it was about her car anyway. She quickly typed in her digits and name and handed his phone back to him.

Great. I’ll see you later” he smirked, trying not to sound excited at seeing her again.

“Yeah, see you there” she replied, as she quickly got out of the car and walked towards the entrance.

Dean watched Y/N walk away, appreciating the way her hips swayed as she walked. He told himself it was harmless to look. It’s not like he was going to do anything about it. He quickly pulled away from the curb, the engine roaring as he drove to the garage.

* * *

Later that day, just after lunch, Dean left the garage with Benny in charge until he got back. He drove back to his street and stopped in front of Y/N’s driveway with the tow truck. He got out of the truck and walked over to her car, popping the hood open. Given the sound he could hear that morning when she attempted to turn the car on, it was clearly the starter and the flywheel that weren’t cooperating with each other. He opened the driver’s side door and put the key in the ignition. When he turned it, he heard the same sound, which confirmed what he thought. The grinding noise also seemed to die down every quickly, which meant the battery was weak, too. Hopefully there was enough in there to get the car into neutral for a tow.

He spent a few minutes trying to get it to start without harming the flywheel, which already looked to have some broken teeth. He got out of the car and walked over to the tow truck, driving it up the driveway. He slid the panels under the back wheels, and then got out to put Y/N’s car in neutral. Once everything was secure, he got into the tow truck and drove back to the garage.

As he drove, his mind wondered to Y/N. The conversation he had with her that morning was so easy, and they had just met last week. It wasn’t that easy with Lisa. Having been with Lisa for 3 years now, shouldn’t they have their easy moments, too? The first year had been great. The second was a little rocky, with its fair share of arguments and apologies. Soon after, as he quickly started to realize the kind of woman Lisa was, he knew the charade was over. She was a great mom to Ben; it was everything else that was a problem. The last year had been filled with distant behavior and more arguing, a lot arguing. To the point of yelling and not being able to hear what the other person wanted. He also doubted whether she told him the truth about something that was bothering him, but he didn’t dwell on that.

If they weren’t fighting, it was mostly quiet as they’d ignore each other or pretend to be the happy couple when people came over. They had tried to fix things, but it had pretty much been useless for about nine months straight now. Maybe things would be different with Y/N…

Dean shook his head. He couldn’t think like that. Just because things were rocky with Lisa didn’t mean he could check out on her and Ben. He still cared about them and didn’t want to do anything to hurt them.

He arrived at the garage and decided to get his mind off things by seeing what to do about the car. Work was always a good distraction from what was going on at home, and it would have to be a distraction from thinking about Y/N.

Y/N sat in the staff room, munching on her salad. It was a slow day, surprisingly, and so she found herself just scrolling through social media and news articles. She was on top of her work for school, so it was nice to take it easy for one lunch. Her phone chimed loudly, showing her she had a message. As she opened it, she smiled down at the screen.

_Hey, it’s Dean. Just got back to the garage with your car. Pretty positive I know what’s wrong, but I’ll tell ya when you get here._

She instantly replied back.

_Thanks so much for doing this. I really owe you!_

His reply came quickly.

_You really don’t, sweetheart! That’s what friends do :)_

_So… we’re friends now? I thought we were just neighbors._ She typed back, with a laugh emoji.

_You knew I had an Impala. Trust me, we’re friends ;)_

She couldn’t help the smile that spread across her face. She bit her lip trying to keep it at bay, but she just couldn’t.

She and Dean were friends now. Maybe that would help in keeping her crush on him from becoming complicated.

* * *

“Thanks for doing this” Y/N said, as she sat in the passenger seat of her friend’s car.

Cas smiled, waving her off. “You’re welcome. I should really see the guys anyway. I haven’t in a while now.”

“I didn’t realize you were friends with Dean” she said, trying to act casual. She was dying inside knowing that they were friends. It was like she couldn’t escape him. Not that she wanted to, even if she should.

“Yeah, since high school” he nodded, as he glanced at her. “We drifted a little when I went to college in California and he stayed here, but we reconnected once I got back. I’m friends with most of the guys who work there.”

“That’s great” she said and looked out the window. Hearing how close he was with his people made her miss her people.

“So, how long have you and Meg been together?” she asked, changing the subject from Dean.

Cas smiled as he thought about his girlfriend. “4 years. I never thought she’d go for me, so I know I’m lucky to have her.”

She smiled sadly, longing to have something that would last more than a year and a half.

“I was telling her about you, and she wants to meet you as soon as possible” Cas laughed.

Y/N joined in and nodded. “I do too.”

Cas pulled up to the garage and Y/N could feel her nerves flutter around like butterflies in her stomach, as she stared up at the sign _Winchester’s Auto Repair_. Dean had that effect on her, and it was scary to think how quickly she had started to like him. The reception area was closed, so they went in through the side door, after Cas shook the front door and found it locked. She walked into the garage, with Cas behind her, instantly hearing buzzing noises in the corners of the garage. She looked around and tried to spot Dean, but was met with a muscular man, short hair and a beard, wearing a white Henley, smiling at her as he walked over.

“You must be Dean’s neighbor” he said, his Southern accent, mostly likely Louisiana, thick and raspy. His blue eyes shined as bright as his smile. “I’m Benny.”

“Y/N” she smiled in return.

“Hey brother” he said to Cas, nodding at his friend with a smile.

He looked at Y/N, the smile never leaving his face. “I’d shake ya hand, but as ya can see” Benny laughed, showing her his greasy hands. “Dean’s just on a call, he’ll be out soon.”

“Okay, great” she said, but just as she did, she saw Dean coming out of the office.

“Hey!” he beamed, as he walked over. “I see you’ve met Benny.” He patted his Cajun friend on the back as he stopped by him.

“Hey man” he said to Cas, as he hugged him. He smiled at Y/N, and she felt as if her heart skipped a beat.

“Your car’s out back. You wanna come with me and we can talk?” he asked her.

“Sure” she replied. She turned to Benny and smiled. “It was nice meeting you.”

“Good to meet ya, cher” he winked at her, causing her face to heat up.

Dean rolled his eyes as he led the way, walking past his friends. “Ignore him” he told Y/N, causing Benny to snicker when Dean was out of ear shot.

Y/N followed behind Dean, as they walked past all the cars inside the shop. They went out to the back, which was a small outdoor workstation, with a few more cars out there. She spotted hers as they walked over.

“Okay, so…” he started as he popped the hood on her car. “The starter wasn’t catching on the flywheel because it had broken teeth, that’s what the grinding noise was. And the noise was sort of dying as well, so the battery’s weak.”

Y/N looked at him blankly, her eyes wide as she tried to understand what he just said. Dean found it extremely cute.

“All I understood was the battery part” she shrugged; her eyebrows furrowed.

He let out a small chuckle. “It’s okay, I forgot that you don’t understand car speak.”

“Guilty” she confessed.

“Don’t worry about it” he reassured her. “Basically, you’re looking at two new parts, which I’m gonna have to put an order in for and uh… it’s gonna cost ya some.”

She sighed heavily, hanging her head. “Great.”

“Hey, it’s all good. I’m gonna do it for half” he told her, with a smile.

Her head snapped up in shock. “No, Dean, I’m not asking you to do that.”

“You don’t have to; I’m doing it anyway. The only thing is, it’s gonna take a week for the parts to get here, so you have to do something about getting places. There’s a good car rental over on-” he explained but she cut him off.

“That I can deal with it, but Dean… I can’t-” she stopped when he gave her a playful glare.

“It’s not up for discussion, Y/N” he stated as closed the hood. He crossed his arms as he leaned against the car. He looked at her and she just couldn’t take it anymore. Damn him and his glorious face for being such a nice guy.

“Dean” she sighed, shaking her head.

“Y/N” he said, smirking.

A silence fell between them as they looked at each other. He wasn’t going to budge on this, so she had to admit defeat.

“Thank you” she said, smiling.

“No problem” he said, still smirking.

Y/N had noticed he said that every time she thanked him so far. It almost like their thing, now. Shit. They had a thing already.

She smiled and leaned into him, wrapping her arms under his as she hugged him. Dean was a little startled but quickly wrapped his arms around her shoulders. He smiled as the smell of her shampoo filled his nose, just as the scent of his deodorant mixed with a hint of motor oil smell filled hers. They both realized that the hug had lasted longer than they expected it to, and quickly pulled away from each other.

“Alright” she moved a few steps away from him, pushing her hair back, awkwardly. “I better head home.”

Dean scratched the back of his head, trying not to think about that hug. “Yeah, I gotta finish up and pick up Ben” he moved off the car and walked her back out. It was quieter in the garage now, and Y/N could hear _Back in Black_ playing from the little speakers in the corners of the garage.

She looked around the room, trying to decide whether she should ask him what she wanted to, before looking back at him.

“Hey, if you’re not doing anything tonight… you want to come over for an early dinner? It’s a school night, I know but I can at least pay you back in food” she asked.

Dean looked at her but didn’t say anything. Y/N realized how that must’ve sounded and immediately back tracked.

“Oh, I mean you and Lisa. Both of you. Not just you, both of you” she rambled.

Dean laughed and patted her arm. “It’s okay, Y/N. Uh, yeah. I mean, I’ll run it by her, but it shouldn’t be a problem. Is that allowed though?”

She knew what he was asking and nodded. “As long as we don’t talk about Ben or any of my other students, it’s fine. I mean, this is a small town. Who else are we supposed to socialize with?”

“Well, he’s going to be over at a friend’s anyway, working on a project. So, coming over to yours will be better than being at home. It uh… gets quiet when he’s not around” he told her, but quickly realized how much he revealed.

Y/N realized what he meant but didn’t say anything. “So, I’ll see you both tonight.”

“Sure thing” he nodded.

Y/N smiled and walked away. Cas insisted on taking her home, but she told him she’d be fine to walk. It wasn’t that far. Dean watched as she said goodbye to both his friends and took her things out of Cas’s car, walking down the road. She had an effect on him, and it was beginning to scare him. He was in a relationship and had made a commitment. He couldn’t just back out because he wasn’t happy. He had to try harder and make more of an effort, and he had tried when they started going through problems, but that hadn’t been enough for Lisa.

Maybe he had to try again.

* * *

“I really don’t like this” Lisa lamented, as she fixed her top in front of the mirror.

Dean rolled his eyes, annoyed at her attitude. Ever since he told her that Y/N had invited them for dinner, she had been voicing how unsure she was of going over there.

“Lis, if you’re having a tough time with this then why’d you say yes in the first place?” he asked, as he shrugged on a fresh plaid shirt.

“Because…” she didn’t really have an answer. “I don’t know, I just agreed because she’s new here and she needs people to talk to, clearly.”

“She’s not desperate, Lisa” Dean turned to glare at her. “You’re talking about her like she doesn’t know how to make friends. Plus, she literally just got here.”

“I didn’t mean it like that” she corrected herself.

“Well, that’s sure as hell what it sounded like” he clipped back. “Not everyone has to be out every damn weekend to prove they have a social life.”

“What’s that supposed to mean?” she asked, frowning.

“Nothing” he mumbled. “Let’s just go.”

Dean turned and walked out of the bedroom, picking up his jacket along the way. He waited for Lisa to pick up her bag, before he walked out of the house, with her locking the door behind them.

Y/N leaned against the kitchen counter, a glass of wine in front of her. She never drank on a school night, but she really needed at least a glass before her company for the evening arrived. She was nervous to have Dean and Lisa over to her house, mostly because of Dean. She was really crushing on him and she had to hope that she could stop herself from looking over at him in a way that would make it obvious how she felt. At least with Lisa there she could control herself. _Fake it till you make it, Y/N_ she thought to herself as she took a big gulp of wine.

When she got home, she had made chicken alfredo for dinner, something that she knew how to whip up quickly.

Y/N jumped out of her skin and her thoughts, as the doorbell sounded. She smoothed her hands down her jeans and fixed her plaid shirt as walked to the door, opening it. She smiled as she saw Dean, trying not to linger on him as he smiled back at her.

“Hey guys, come on in” she said as she looked at Lisa.

She stood aside and let them in, closing the door.

“Wow, looks a lot different without all the boxes” Dean joked, as he walked into the living room.

“Wait…” Lisa stopped next to him, a look of confusion on her face. “You’ve been over before?”

Y/N sensed that Dean didn’t tell her about that and stepped in. Dean didn’t need to be interrogated for something small. “Oh, he just helped me on the first day here, with some of the furniture.”

Lisa nodded. Luckily, she let it go, but still walked past Dean with a glare.

“So, can I get you guys anything? I’ve got beer, wine, iced tea…” Y/N listed but Lisa shook her head.

“I’m fine, thanks” she said, simply.

“Dean… beer?” she asked, with a small smile.

“Sure, thanks, Y/N” he replied, giving her a reassuring smile.

“Well, dinner’s actually ready so we can sit down. I’ll bring your beer over” she said, walking into the kitchen.

Dean and Lisa sat down at the table, next to each other. Y/N took a beer out of the fridge and brought it over to the table, setting it next to Dean’s plate. She sat down across from him and lifted the lid off the dish on the table.

Dean whistled, a dreamy look in his eyes. “That smells amazing, Y/N.”

“Thanks” she laughed. “Let’s hope it tastes good.”

They all served themselves and dug in, and surprisingly, Lisa was the first complement her.

“This is really great, Y/N” she said, after a mouthful.

“Thanks, Lisa” Y/N smiled.

“This is amazing” Dean hummed, around a mouthful. Lisa glared at him, but Y/N found it endearing. He noticed Lisa looking at him and swallowed quickly.

“So…” Y/N started. “Dean told me how you guys met. I think it’s amazing that you reconnected, and now here you are” she smiled, as she looked at Lisa.

Lisa looked at her, her lips pursed as she took in what Y/N just said. “Yeah, it’s pretty great, but um… you know it’s private so…”

Y/N nodded, staring down at her food. “Of course. Sorry.”

“It’s fine” Lisa played it off with a small smile.

As Lisa ate, Dean looked up at Y/N with an apologetic look. He mouthed ‘sorry’ to her and she smiled, shaking her head to tell him it was okay.

“So, Lisa. What do you do?” she asked, changing the subject.

“I’m an accountant” Lisa told her. “Not the most interesting of jobs, but hey, at least the money’s good.” She added in, with a small laugh.

The conversation remained simple and somewhat bleak. Mostly questions about work and brief questions about family, that didn’t require a lot of explanation. It was a civil evening; however, which Y/N was really grateful for. When they were finished, Y/N picked up the dish and started clearing up.

“Hey, Y/N. where’s your bathroom?” Lisa asked, as she got up from the table.

“It’s just down the hall on the left” Y/N instructed.

“Thanks” Lisa muttered as she left the room.

When she was out of ear shot, Dean stood up and helped Y/N clear the plates. “I’m sorry, Y/N. She just-”

“Dean, it’s really okay. Please, don’t apologize” Y/N reassured him as she walked into the kitchen.

She carried the plates over to the sink and didn’t realize that Dean was right behind her, ready to pass the glasses over. She turned around and smacked into his chest. She laughed as he held her steady, joining in.

“Sorry” she continued to laugh.

“It’s okay” he laughed as well, as his hands rubbed along her arms.

Y/N looked up at Dean and realized he was looking at her. Their eyes met; their bodies close to each other. Dean looked down at her lips, beautiful and inviting. She looked up at his, perfect and pouty, begging to be kissed. It would’ve been easy to lean down and press his lips against hers, but they couldn’t. As much as he wanted to, he couldn’t. They heard the bathroom door open down the hall and jumped apart. Dean went back to the table and pushed the chairs in, making it look like nothing had just happened.

Lisa walked back into the room, oblivious to what had happened just moments before. She smiled as Dean stood next to her. She put her arm around him and smiled up at him. Y/N looked away, her heart sinking at the scene in front of her.

“Dinner was really amazing, Y/N. Thank you” Lisa told her. “We should really get going, though. I’m sure Ben’s on his way home, too.”

“Of course,” Y/N walked over to them. “Thanks for coming.”

“Thanks for having us” Dean said, trying not to look directly at her.

Y/N walked them over to the door. “Goodnight.”

They both called out ‘goodnight’ as they walked down the steps of the porch. Dean knew he couldn’t look back at Y/N, so he kept walking, resisting the urge to turn around.

Y/N shut the door and leaned her forehead against the wood.

“Fuck” she whispered, as she closed her eyes and shook her head.

That was too close. She can’t believe she almost did that with Dean. That couldn’t happen again.

She began to realize that maybe her little crush on him was developing, and that was a scary thought that she didn’t want to entertain. She couldn’t.

So, she wouldn’t. It would be easy enough. She just had to avoid him.

That was easier said than done.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	4. A Lesson in Self Control

**Summary for the Chapter:**

> After Charlie witnesses the looks between Dean and Y/N outside the school on Friday, she convinces Y/N they should go out for drinks. At the bar, Charlie and Y/N bond, as she opens up to Charlie about Dean but also her past. After several drinks, Y/N goes home drunk and gets a little help from a friend. The next day brings a little embarrassment, but also brings up feelings within Dean and Y/N, that they know they shouldn’t be feeling.

**Notes for the Chapter:**

> Warnings: Swearing, Alcohol Consumption, Mentions of cheating, Mentions of reader’s ex, Talk of Emotional Abuse, Mentions of a physical incident against reader, Drunk reader, Embarrassment, Dean being sweet (yes, that’s a warning), flirting, forbidden feelings

* * *

Y/N took off her red glasses, smiling as she looked at her students. She could see them all flicking their eyes up at the clock every now and then, wondering when the bell would ring. She found it amusing as she tried not to laugh. It was Friday and they couldn’t wait to get out of there and start their weekend fun. She couldn’t wait herself, hoping to have some time for herself, call her family and maybe go see a movie.

Unfortunately for her students, they still had some time before they could leave, using that time to take the notes for the criteria set for their book reports. She watched as they all scribbled in their notebooks hurriedly, wanting to get out as soon as the bell went off.

“Make sure it’s personal to you” she told them as they wrote. “Books have a way of really affecting us, so I want you guys to choose something that really had a big effect on you.”

Some of them mumbled an “okay” while others nodded.

Suddenly, the bell rang, and they all sprung up at the same time. It was like how smaller children got excited for ice-cream.

“Alright, don’t all head out at the same time! You’ll plow each other out of the way!” she laughed.

“Sorry, Miss Y/L/N” one student called out.

“Have a great weekend, guys!” she called out in return.

Y/N walked out of the room as well, following them down the hallway and out of the school building. She smiled as students were being picked up by their parents, getting on the bus home or their bikes and riding home. She spotted a parent of one of her students notice her, walking over to her.

“Miss Y/L/N?” the woman asked.

“Yes” Y/N smiled, offering her hand.

“Oh, it’s wonderful to meet you, I’m Carol. Amy’s mom” she said, shaking Y/N’s hand.

“Wonderful to meet you, too” Y/N agreed.

“I just wanted to come and introduce myself and welcome you” Carol said, a bright, peaceful smile on her face. “I know it’s already been a couple of weeks, but I hope you’re loving Lawrence.”

Y/N nodded. “I’m definitely warming up to life here.”

“Well, Amy’s really fond of you. English is already her favorite subject but she’s so happy to have someone like you teaching it” Carol complemented her.

Y/N beamed, her heart soaring. It was always great to hear when kids enjoyed a subject and the way you taught it.

“She’s a great student, so that definitely makes it easy” Y/N told her.

Carol blushed, delighted by the complement for her daughter. “Well, we better go. I’m sure we’ll see you around.”

“Of course,” Y/N said. “It was great to meet you.”

As Carol walked away after saying goodbye, Y/N looked around as the crowds of children started to clear. She spotted Charlie and was about to walk over, when she noticed who she was talking to. Dean was leaning against his car, aviators on and laughing at something Charlie just said. Ben was sitting in the car, waiting for Dean. She didn’t realize that Charlie knew Dean too, but she really should’ve made the connection considering she knew Cas, and Cas knew Dean. She thought about going over there, but she didn’t want to interrupt them. Plus, after what happened the other night at dinner with him and Lisa, she wasn’t sure if she should go over there.

“Y/N!” she heard her redheaded friend call out and she knew she had to go over.

She smiled as she walked over, trying to prepare herself to be near Dean again. He looked so damn good in that moment, and she was finding it hard to look at him.

“Thanks to your car, I know you already know each other, so I don’t have to introduce you” Charlie laughed, as she nudged Y/N with her hand.

“Yeah.” Dean took his sunglasses off and Y/N saw that he was looking directly at her. She was suddenly nervous again.

Dean took her in, dressed in a black dress that hugged her body in just the right way. Her red glasses were tucked into the neckline of her dress, and he had a sudden urge to see her wearing them. _Mind outta the gutter, man_ he thought to himself as he looked away from her.

“I didn’t realize you guys were friends” she said, as she stood in front of Charlie and Dean.

Charlie smiled as she looked at Dean. “Yeah, have been for years.”

“Charlie’s like the little sister I never wanted” Dean teased, smiling cheekily at her. Charlie punched him in the arm, and he laughed.

His gaze moved from her back to Y/N. He hadn’t been able to get her out of his head since the first time he met her, but even more so after what happened at her house.

Charlie noticed how Dean and Y/N were looking at each other and dropped her head, smiling without them seeing.

“I better go” he said, suddenly, putting his sunglasses back on. “Lisa finished work early and we’re going to Sid and Olivia’s for dinner.”

“Tell them I said hi” Y/N told him, trying not frown as she wished he had stayed longer.

“Sure thing” he nodded. He moved in to hug Charlie, kissing her head.

Y/N watched as Dean got into the car and drove off, the car roaring down the road. She turned to Charlie and her face dropped into a frown, when she saw her friend grinning at her.

“What?”

“You like him” Charlie stated.

Y/N stared at her in shock, before scoffing a laugh. “You’re insane.”

“On the contrary, I’m completely sane” Charlie countered. “And you denied it a little too quickly, so it has to be true.”

“Charlie…” Y/N trailed off, not knowing how to respond to that.

“I think we need to get a drink together” Charlie suggested. “We haven’t gotten a chance to hang out outside of work yet.”

Y/N grinned. “Sounds great.”

“Tonight?” Charlie asked.

“Name a time and place, and I’m there” Y/N responded quickly. She was excited to go out and see what Lawrence was like on a Friday night. She knew it wouldn’t be much for a small town, but she also knew she needed to know how the nightlife was here.

“Ditch the rental at home and I’ll pick you up” Charlie said, as she started to walk away. “I’ll be there at 7!”

“See you soon!” Y/N called out as they both made their way back in to collect their belongings, before they headed home.

* * *

When she got home, Y/N relaxed for a while before she needed to get ready. She freshened up and got dressed into black ripped skinny jeans and a dark mustard sweater. She put on her black heeled ankle boots, ran a straightener through her hair quickly to get the kinks of the school day out and applied light make-up. She picked up her black leather jacket and her bag, just in time when she heard two quick honks of a car horn. She picked up her keys and walked out, closing the door behind her. She walked down the porch steps and smiled at Charlie as she walked over, getting into the car.

Y/N and Charlie made their way to the town square, lined with shops and some restaurants. Deciding they were hungry too; they grabbed a quick bite to eat. Conversation over at the diner mainly consisted of work and minor things, because Y/N had a feeling Charlie wanted to talk about personal things over drinks. After they ate, they walked down the street and past a couple of dive bars, the loud music and chatter filtering out to the streets. She felt better knowing there was something going on in this town and that it wasn’t as sleepy as a place like Rhinebeck. Though Rhinebeck did have its own charms.

Y/N followed Charlie, arriving at the place where they sat at the bar. She and Charlie sat on the bar stools, the bartender immediately coming over to them.

“What can I get you, ladies?” he asked, smiling at them.

“Gin and tonic, please” Charlie replied, smiling back.

Y/N thought it over for a second before she replied. “A vodka martini.”

“Sure thing” he muttered before moving down the bar to mix the drinks.

Y/N and Charlie both took their jackets off, settling in. The bartender put their respective drinks in front of them and then went to serve other customers. Charlie picked up her glass and turned to Y/N.

“To surviving your first two weeks” she said, smiling.

“Well, thanks for making it easy for me to settle in” Y/N smiled back, clinking her glass against hers. “I really mean it. You and Cas have really helped me and supported me, so… thank you.”

“No need to thank” Charlie waved her off, taking a sip of her drink. “So… let’s get to the real reason we’re here…”

“Oh god” Y/N groaned.

“Oh yeah” Charlie smirked. “You like Dean.”

Y/N laughed a little to herself. She didn’t beat around the bush, this one.

“Yeah. I do” Y/N admitted, feeling slightly relieved to say it out loud. “At first, I really just thought it was a crush, something that would just go away after a couple of days. Then… then the butterflies stuck around and they’re not going away. Every time I see him… I just want to be near him. All the time. I know two weeks is way too soon to be feeling like this about someone I just met, but-” she explained but Charlie shook her head, cutting in.

“I don’t think the length of time matters to Oxytocin” Charlie advised her.

“I’m not quite at the love stage yet. In fact, I hope I never get there because that’s going to get me into trouble” Y/N countered.

“Which is unfortunate because I think you two would be adorable together” Charlie confessed, a guilty grin on her face.

“What?” Y/N scoffed, not quite believing what she just heard.

“I’m sorry, it’s just… the way he was looking at you, even just for a few seconds, I haven’t seen him like that in a really long time” Charlie said, a sad smile on her face.

“Oh god” Y/N groaned, her face dropping into her hands. “Charlie, what are you doing to me?!”

“I know, I know” Charlie shook her head, not knowing what else to say.

“I can’t” Y/N shook her head, taking a large sip of her martini.

“I know, and I wasn’t telling you to go for it at all. I’m sorry” Charlie apologized, sipping her drink.

“It’s okay” Y/N reassured her, patting her back. Once they had both calmed down, Y/N turned to her friend. “Oh, they came over for dinner on Monday. I wanted to thank Dean about the car, and he came over with Lisa.”

“Really?” Charlie asked, a little shocked. “She actually came over?”

Y/N nodded. “Seemed like she didn’t want to be there, though. I mean, she was okay, she didn’t say much, which I don’t really care about, but she was kind of cold with Dean.”

Y/N looked at Charlie and saw that she looked like she wanted to say something but was contemplating whether she should or not.

“Okay, look…” Charlie started, trying to find her next words carefully. “I’m just going to tell you this, and it’s in no way saying that you have to do something, I just think you need to know, now that you’ve brought this up.”

“Okay…” Y/N didn’t know where she was going with this, but she listened anyway.

“Dean and Lisa have never been good for each other. They had a one-night thing, it was great for both of them, but that’s where it should’ve ended. Things were fine at the start, but once they got past the one-year mark, is when things started turning. Two years in, it got pretty bad. I mean, Dean doesn’t know for sure… but he thinks that she might’ve slept with someone else when she went home to visit her family. Things haven’t been right for a while now. Between not trusting her and them fighting at the drop of a hat all the time… it should’ve ended a year ago” Charlie explained.

“Wow” Y/N sighed, shaking her head.

“The only time we see him happy is when he’s at work or when he’s with us and she’s not around. Hell, I don’t particularly think she likes any of us, and we’ve tried really hard to include her. She never really wanted to do anything with us and would only come out with Dean if she wanted to prove things were okay. After a while, we just stopped trying to get her to like us” Charlie went on.

Y/N couldn’t imagine anyone not liking Charlie or Cas. “Seriously?”

Charlie nodded, a glint of anger behind her eyes. “She’s never encouraged him with the business, she’s always put him down for his choice in friends. She claims it’s to make him see that he’s better than them, but she’s just forcing him to think things he never would.”

There was a long silence between them, as Y/N processed everything Charlie just told her. She and Charlie were only just starting to become friends, so she could’ve easily said she didn’t believe her. She did, though. Charlie looked genuinely hurt, which meant everything was true.

“Fuck” Y/N whispered.

“Yeah” Charlie said, raising her eyebrows. “Dean’s generally a happy, care-free guy but for over a year now, I know he’s been hurting. He just hides it behind his larger than life personality. I just want to see him as his old self again. He thinks that if he stays, maybe things will just fix themselves, but they won’t. They haven’t yet and they certainly won’t the longer he stays in this relationship.”

“Wow” Y/N sighed again.

“So, that’s all I want to say” Charlie finished. “I’m not saying you have to do anything about it, but I want you know the reality, and maybe not hate yourself so much for having the thoughts you’ve been having.”

Y/N nodded. Hearing it made her feel slightly better, but worse now that she knew what he was going through.

Another silence fell between them as Y/N thought about everything Charlie said.

“It scares me” Y/N looked down into her glass, shaking her head. “Feeling something so quickly for someone I just met. I’ve never felt a connection like this before. Not even with Ethan.”

“Ethan?” Charlie asked, confusion written on her face.

Y/N bit her lip. She didn’t realize she had never mentioned him to Charlie. “My ex.”

Charlie nodded slowly, immediately understanding. “I’m guessing things didn’t end well if you’re so far away from New York.”

“No, they did not” Y/N muttered after a sip of her drink. “He uh… he was really controlling of me. He’d tell me how I shouldn’t dress up and be too revealing, but then somehow… somehow, he’d tell me that I didn’t try hard enough either, that I wasn’t attractive enough. My job wasn’t good enough. I… I wasn’t good enough. I didn’t… I didn’t think it was something that was a problem, no matter how much anyone told me it was. I thought he’d… he’d say the things he did because he just wanted me to be better, but it was to stroke his own ego.”

“Scumbag” Charlie muttered; her face morphed into anger.

“Yeah” Y/N laughed, bitterly. “I couldn’t see it until the night he hurt me. I thought he was doing those things because he loved me, but love isn’t making a person hate themselves to make yourself feel better.”

“You said he hurt you…” Charlie trailed off, worried that she’d uncover feelings that Y/N had buried.

“Just once, he pushed me and I ended up in hospital with a concussion” Y/N said, her words choking around the lump in her throat. “Once I was better, my parents helped me get my things out of his apartment. It wasn’t an easy transition; I kept seeing him everywhere. I tried to get a restraining order against him, but his family had money and probably paid someone off, so he never got charged with one. He eventually left with his new girlfriend, but that didn’t mean it got better for me. It took some time, a year of therapy before I left, but I realized that I wasn’t going to let anyone do that to me ever again. That place… I didn’t want to leave my family but there was too much of him there. So… now I’m here.”

“I’m glad you are. Y/N, you’re… shit, you’re fucking amazing and I hate that someone made you feel like you’re not” Charlie said, quietly, her eyes watery.

“I really know how to tell a story, huh?” Y/N jested, trying to lighten the mood again, as she blinked to keep her tears from falling.

“I’m glad you told me, that you could trust me with that” Charlie said, a small, empathetic smile playing at her lips.

“I’m sorry” Y/N shook her head, feeling awful at her sudden confession of her past. “I shouldn’t have brought it up when we’re here to have a good time.”

Charlie took her hand in hers. “No, please don’t apologize. I really am glad that you did. I’m so glad I know you.”

Y/N smiled at her. She knew Charlie would hear the story and wouldn’t pity her but be there for her and listen. She held Charlie’s hand, squeezing it. She was glad to have met the woman sitting in front of her.

“You know… Dean would never do that to you, right? To anyone” Charlie told her.

Y/N nodded, closing her eyes. “I know. I don’t know how I know, but I just see him, and I know that he’d never do that.”

“And that’s what scares you, right? That he’d never do that, that you feel so much and that he’s with someone else?” Charlie asked.

Y/N looked at her and didn’t say anything. Her face said it all. Charlie just nodded, before taking the last sip of her drink.

“I need another drink” Y/N said with a small chuckle, having finished her martini.

Charlie just smiled as she flagged down the bartender.

Another drink turned into two more after that. Y/N understood what Charlie said clearly, but that didn’t mean she was going to take the words and run with them. Why risk everything on what could just be a crush? She was wrong, 2 weeks was absolutely a ridiculous amount of time to suddenly fall for someone. She was overthinking things.

She was thankful when Charlie dropped the subject of Dean, having said what she needed to about how she felt towards Lisa, knowing Y/N would interpret everything the way she needed to. She also felt a huge pressure lift off her chest when she told Charlie about what happened with Ethan. It had been a year since the break-up and since she had started therapy. Her last session before she left had left her feeling relieved. Coming to Lawrence had been the best decision, even with her situation with Dean. Charlie was amazing and was glad she spoke up and told someone who she really trusted.

They eventually moved onto talking Charlie and Dorothy and Y/N found the redhead incredibly cute in that moment, as she gushed about her girlfriend.

Y/N knew that once the fourth martini went down, she had to get home. She was well and truly drunk and all she wanted to do was sleep it off. Just forget them ever talking about Dean.

As they left the bar, she stumbled slightly as they walked down the road. She needed to get an Uber and be alone in her thoughts now, her mind reeling with their conversation but vodka, too.

“Are you sure I can’t take you home?” Charlie asked, concern all over her face.

Y/N chuckled as she shook her head. “I’m sure, I’ll be fine.”

“Okay” Charlie agreed, reluctantly. “Message me as soon as you get home.”

An Uber quickly pulled up a few moments after she called it, and Y/N got in. She smiled and waved at Charlie. “Thanks for tonight.”

“You’re welcome. I’ll see you Monday” Charlie smiled.

* * *

Y/N leaned back against the seat, looking out the window. She really didn’t need man drama while she settled into a new town. She had had enough of it back home in her previous relationship, that one almost ruining her mental state. She was still recovering, even if had been a year since they broke up. Memories of him and imagining him around town, even after he left, were what made her decide to leave too. The last thing she needed was to be with someone. That being said, someone could argue with her that it was time to move on and find something better, something more meaningful.

Well, that something would have to come from somewhere else because it sure as hell wasn’t going to come from Dean. As much as she was attracted to him, he was with someone. No matter how unhappy the relationship was. Her mind floated to something Charlie told her. That it was possible that Lisa cheated on Dean.

He was sweet and caring, nurturing and compassionate. Gorgeous as hell and insanely hilarious. Who could ever cheat on him? People had their flaws, but that didn’t mean you give up on a person. His flaws couldn’t be as bad as her ex’s.

The Uber pulled up outside her house. Y/N steadied herself as much as she could as she got out. The car pulling up caught the attention of Dean, however, as he was sitting on the front porch, beer in hand. He watched as Y/N stumbled up the stairs of her porch and tried to open the door to her house.

Dean put his beer down on the stoop and got up from the stairs, walking across the street. As he walked up her porch stairs, Y/N turned around and smiled at him, indicating to Dean that she was quite drunk.

“Dean” she slurred happily, her eyes sparkling.

He tried not to laugh as he walked over to her. “Doing okay there, sweetheart?”

“Sure am” she giggled in her drunken state. “Just trying to get my door open.”

Dean watched as she tried to put the key in but kept missing the keyhole. He stepped forward and took the key from her hand, putting it into the lock and opening the door with ease.

“Thanks” she beamed.

As she went to walk through the threshold, her foot caught the edge and she stumbled. With quick reflexes, Dean caught her arm and pulled her into his body.

“Whoa, Y/N” he exclaimed, cradling her to his body.

She let out a loud cackling laugh, completely unaware of her near injury. Knowing that this wasn’t going to end well if she kept at it by herself, Dean bent down and lifted her legs up as he cradled her body. He lifted her into his arms as he carried her into the house, trying not to dwell on how good she felt in his arms.

“Ooh” she gasped, as her arms wrapped around his neck. “You’re very strong, Dean.”

She couldn’t help but lean her head on his shoulder, the intoxicating scent of cologne driving her crazy.

He ignored that as he walked down the hallway and into her bedroom.

Dean gulped as he looked around, the realization that he shouldn’t be standing in her bedroom hitting him suddenly. He quickly walked to the bed and laid her down, watching her eyes flutter as the alcohol she had consumed took control.

“Have to… have to text Charlie” she mumbled, the alcohol making her sleepy.

 _Ah, so that’s who she went out with_ he thought as he took off her shoes and pulled the covers over her.

He picked up her bag and fished around quickly, finding her phone. He didn’t look in, knowing that a woman’s handbag had things in there he had no business seeing.

Y/N unlocked her phone and handed it to him, flinging her head back to her pillow.

Dean bit back a laugh as he messaged Charlie as Y/N.

_Hey, made it home safe. Thanks for tonight._

He added that in because if she was this drunk, then clearly she had a great time with his friend. Who wouldn’t?

Dean placed her phone on the nightstand and was about to walk away when he heard her stir.

“You’re really sweet, Dean” she mumbled, only one eye looking up at him as her face was smooshed to her pillow. “Why can’t all guys be like you?”

Dean shook his head. She was really out of it. “I wouldn’t say that, Y/N. I’m not someone to be compared to.”

“I think you are” she said, a soft smile on her face. “I think you’re something special, Dean Winchester.”

A smile spread on his face, but it dropped quickly. She wouldn’t remember saying it in the morning, so it was best not to dwell on it.

“Goodnight, Y/N” he whispered.

“I could get used to you in my life” she whispered, as she drifted off into slumber.

Dean felt a pang in his heart at her words. She may have been drunk, but it had been a while since someone had something like that to him. He couldn’t let her words affect him like that, though. He was with someone else and he needed to make that work again.

Dean slowly walked out of her room and back down the hall. He took out his wallet and took out the Advil tablets he kept in there, leaving them by her coffee machine. He picked up a napkin and quickly scribbled a note on it, before leaving her house. Hopefully she wouldn’t remember all of that in the morning and they could avoid the awkwardness that would follow.

* * *

The sunlight from the windows streamed into Y/N’s room. It warmed the covers she was wrapped in, causing her to stir. She groaned as she lifted her head, feeling the heaviness of last night’s drinking session with Charlie. She sat in bed as she tried to recall what happened last night. Her eyes widened as she remembered, everything quickly rushing to her head.

Dean had helped her into the house. Dean had most likely helped her into bed. Dean had been in her bedroom.

She couldn’t remember if any words had been exchanged. Had she said anything that would cause her embarrassment?

Y/N slowly got out of bed and picked up her robe, wrapping it around herself. She picked up her phone and walked out of her bedroom, into the kitchen, as she needed coffee as soon as humanly possible. She looked at the time. It was 10 in the morning. She had really been knocked out last night. She walked over to her coffee machine and was about to start filling it, when she noticed something out of the corner of her eye.

A slip of Advil tablets and a note laid next to the machine. She smiled as she picked up the note, scribbled in all-caps.

**HOPE YOUR HEAD DOESN’T HATE YOU TOO MUCH IN THE MORNING.**

**-D**

Her stomach flipped as she bit her lip, reading over the note again. She liked his handwriting. It said so much about him.

She quickly took the Advil before she made her coffee and breakfast, two eggs and a little bacon. You had to have bacon on a Saturday morning, especially if you were hungover. That’s what she felt.

The rest of her afternoon consisted of paying bills and doing some work for her classes, once her head was feeling slightly better. She made a mental note to actually go see a movie next week with Charlie. Maybe they could invite Cas’s girlfriend along, as she was dying to meet Meg. After doing her work for the day, she decided to do a little baking. Saturday afternoon baking was something she did often back home, and she wanted to keep that going here in her new house.

Y/N decided on making an apple pie, one of her favorites. As she got all the ingredients together, she decided to make two, wanting to take one over to Dean as a thank you for helping her last night. Hopefully he liked pie. She turned on one of her softer playlists, as cooking or baking needed some kind of music in the background and something soft was good for her head right now.

An hour later as The Lone Bellow graced her ears, she took out two beautifully golden pies from the oven. She put them on the kitchen bench and went to shower, having still been in the same clothes from last night.

Once she was freshened up, she walked out in dark blue skinny jeans, a white tank top and a pink and white plaid shirt over the top. She took a red and white checked cloth and wrapped it around one of the pies, making sure it stayed warm as she walked over. Slipping her phone into her back pocket, she shrugged on a light jacket to shield her from the light breeze. It was starting to get colder and she wondered what winter would be like here.

Y/N left her house and walked over to Dean and Lisa’s, pie in hand. She was a little nervous and hoped that Lisa wouldn’t be there, so that she could talk to Dean alone. She was slightly ashamed of herself; he was technically a parent of a child she was teaching, and he saw her drunk. She really hated herself for it and hoped that they could talk and come to an understanding.

She quickly walked up the porch steps and rang their doorbell. She waited patiently for a few seconds, before she rang the bell again. Again, she didn’t hear anyone coming for the door. Even the Impala wasn’t in the driveway. They had probably gone out as a family. As she walked back down the porch steps, she heard some music and clinking sounds coming from the back of the house. Wondering if maybe Dean was at home, she walked around the corner to their backyard, the sounds of Metallica’s _Wherever I May Roam_ becoming louder as she got closer. The sight that greeted her caused her eyes to widen and her heart to beat wildly in her chest.

Dean was leaning over the engine of his car with the hood open. He was wearing blue jeans that hung on his hips in the most perfect way, highlighting his cute butt. His dark grey t-shirt defined his physique, the material stretching across his chest and biceps. His arms and face were covered in grease from the car, but that only added to the hotness he was showing at that point. When he turned around and noticed her, he smirked which just killed her dead on the spot.

“Hey, I didn’t hear ya coming out here” he said, walking over to her, turning the music down a little as he walked past his little radio.

She blinked a few times, trying to get out of the trance he put her in. “I rang the bell a few times but then I heard you out here.”

He nodded as he jerked his head towards the car. “Yeah, I gotta work on her from time to time, make sure she’s still runnin’ properly.”

“Well, she’s gorgeous. I wouldn’t want her to fade away either, if I was you” she smiled.

He smirked as he looked at his priced possession. “Dad would tear me a new one if I ever did.”

She laughed a little before a silence fell between them, only the sounds of the song being heard.

_And the road becomes my bride  
And the road becomes my bride  
I have stripped of all but pride  
So in her I do confide  
And she keeps me satisfied  
Gives me all I need  
And with dust in throat I crave  
Only knowledge will I save  
To the game you stay a slave_

Now was as good a time as to bring up what she needed to.

“Dean, I just wanted to say thank you for helping me last night” she started but he waved her off.

“Don’t mention it, sweetheart” he smiled.

He really had to stop calling her that if she was ever going to get anywhere with this. If only he knew what that did to her.

“I know it might’ve felt like just a nice gesture, and it was, but… Dean, I’m really ashamed and I really, really hope you don’t see me differently now” she confessed.

Dean frowned, not sure what she meant. “Why would I do that?”

“It’s just that… I’m a teacher, and I’m supposed to be a certain way. You’re practically a parent to a child in my class, and you shouldn’t be seeing me like that, like how I was last night-” she rambled but the feel of his hands on her shoulders stopped her.

“Y/N, it’s really okay. I’d never tell anyone about that. I mean, shit. You gotta let loose once and a while, too. Maybe someone else would judge you for that, but I never would” he told her, his voice calming her.

“But-” Dean shook his head when she protested.

“Honestly, Y/N. It’s fine. That’s just between you and me. Okay?” he reassured her.

She sighed in relief. “Okay.”

“Good” he winked at her.

Her lips pressed into a thin line as she looked down, trying not to think about that wink.

“It’s just… I didn’t say anything stupid to you, did I? If I did, I’m so sorry” she apologized.

Dean remembered everything she said last night. It had kept him up for an hour and a half as her words circled around in his thoughts.

“Nope” he lied. “Though you did mutter something about finding Christopher Walken sexy.”

Y/N eyes widened. “What?!”

Dean guffawed loudly, shaking his head. “Oh my god, you should see your face.”

She reached up and smacked his arm, causing a small “ah” to leave his lips but he kept on laughing, as he rubbed his arm.

“You’re such an ass” she shook her head, trying not to smile at the sound of his laugh.

His laughter died down as he composed himself. “That was too easy.”

“I don’t think you deserve this pie now” she gestured to the wrapped-up dish in her hands.

His eyes lit up as he looked between her and what was in her hand. “Pie? You-you made me a pie?”

“Yeah, I did, as a thank you for last night but I don’t think I want to give it to you now” she pretended to be upset, riling him up.

“Y/N…” he said, looking her right in the eyes. “Please.”

Jesus. She was putty in his hands. This wasn’t good. She couldn’t do this with him. In that moment, all she could do was hand over the pie with a polite smile. She couldn’t let him think that she was wanted to keep going on this banter of theirs. That was dangerous and she wouldn’t be that person.

She quickly handed it over. “Since you asked so nice.”

His eyes and smile grew brighter, as he giddily lifted one corner of the cloth and smelt the cinnamon and apple.

His eyes rolled back as he moaned lightly. “Damn, that smells amazing. Thanks, Y/N. Seriously.”

“You’re welcome” she said, laughing slightly at his reaction. “I take it you like pie.”

“Like?” he scoffed. “More like obsessed.”

“Good to know” she giggled as she watched him take another whiff. “I better go.”

“Oh, before I forget. Your car should be ready on Wednesday” he told her.

She smiled with a sigh of relief. “Amazing, thank you.”

“So, I’ll see you at the shop on Wednesday” he said, his thumbs rubbing over the cloth around the pie. He was itching to dig into it.

“Yeah” she nodded. “Bye, Dean.”

“Bye. Thanks again” he lifted the pie as he thanked her.

Y/N smiled as she walked away, rounding the corner and disappearing.

As soon as she was gone, Dean walked into the house and put the pie on the kitchen counter. He washed his hands and wiped them down, his mouth salivating as the delicious scent of the pie wafted through the kitchen. He opened a drawer and took out a fork, unfolding the cloth from around the pie dish. He licked his lips he looked down at it, stabbing his fork in and digging up a big bite. He blew on it and shoved it into his mouth. The flavors exploded as he closed his eyes in delight.

“Fuck, that’s good” he mumbled to himself as he swallowed down the mouthful.

It had to be the best pie he had ever had, not including his mother’s because that wasn’t a fair fight. Did Y/N really have to be so perfect that she made an amazing pie, too? How the hell was he supposed to stay away from her if she did things like this?

 _You just have to_ he thought as he wrapped the pie up again, for later. _You can’t keep doing what you’re doing with her._

If this was ever going to remain friendly, then he had to stop turning on the charm, even if that was second nature to him. She made everything so easy. Things hadn’t been easy for him in a long time.

Between what she said in her drunken state to him (she may have been drunk, but she still said it. So, it had to be true, right?) and now bringing him this pie, it was getting harder to resist her. He knew was starting to feel something for her, even if it had only been a couple of weeks. He hadn’t felt like this since the first time he was with Lisa. Once they actually got together, the spark fizzled out quite quickly as comfortability took over. Now, even that wasn’t there.

Maybe it’s only meant to be comfortable. Maybe the spark isn’t meant to stay as you get comfortable with your partner. Though, that didn’t seem right to him. If you were really in love, then wouldn’t the spark stick around?

He had never been more confused about what to do, but he knew what the right thing was. It was to stick it out with Lisa, and that’s what he needed to do.

No matter how much he thought about Y/N.

As Y/N walked towards her house, her smiled dropped. What happened back there wasn’t just a friendly neighborhood chat. That was more. Much more. That was something two people did when they’re getting to know each other as more than friends. That was banter and flirting and messing around with each other with silly jokes. There were looks that made her tingle all over, and polite words that comforted her.

He made everything so easy. What she was beginning to feel for him was so much more than what she had felt before. This feeling wasn’t even there the first time she met Ethan. She knew she was fooling herself when she said this was just a little crush.

As she entered her house, Y/N was determined.

Dean Winchester was not going to have an effect on her.

He just wasn’t.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	5. A Lesson in Not Giving In (Almost)

**Summary for the Chapter:**

> Y/N gets her car back, bringing stability back to her routine. As Friday night rolls around, Dean’s plans with Lisa get derailed as she goes out with her friends. Dean asks Y/N over, resulting in a night of laughs, stories of the past, and something between them that they can’t keep denying.

**Notes for the Chapter:**

> Warnings: Swearing, Talk of past family issues, Mention of reader’s ex, Talk of mental abuse, Neglect, Insecurities, Alcohol Consumption, Dean being cute (yes, that’s a warning), Flirting, Forbidden feelings, Moment of weakness (you’ll see what I mean, I don’t want to spoil it)

* * *

The next couple of days flew by, and before she knew it, it was Wednesday. Y/N was happy to be getting her car back, her life becoming easier again, especially with school. Her classes had been keeping her busy, grading tests and making sure the homework was done. All of her students but a couple were doing well, and she knew she would have to talk to the parents as she soon as they had time to meet. Things remained awkward with Ben, who would never really say much, except for a few sentences each class.

She knew it was hard with her being his teacher and living across the street but given the size of this town it was hard not to see people constantly. The only thing that could be done and what she had been practicing, was not talking about him or to him outside of a school setting.

Cas had brought Y/N into the garage again, once classes were over on Wednesday. Though this time he couldn’t stay, wanting to meet Meg before she started her shift at the hospital. Y/N walked in and was greeted by the receptionist this time, an elder woman.

“Hi, I’m Ellen, what can I help you with?” she asked, a smile on her face.

“Hi, I’m here to pick up my car. I’m Y/N Y/L/N” she told the woman. She had a pleasant demeanor, but Y/N had the feeling she could really get mad of you pissed her off.

“Oh, so you’re Y/N!” she beamed. “Dean’s been talkin’ about ya non-stop. Just making sure he does everything right and on time.”

Y/N felt her cheeks heat up. “Well, that’s nice of him.” Dean had been talking about her to his friends and co-workers? She suddenly felt a little strange to be the centre of attention.

Just as Ellen was about to speak, the door to the men’s room in the reception area opened, and Benny walked out, this time without any car grease on him. He was looking sharp as he was a little dressed up.

“Hey, cher” he smiled, as he enveloped in a hug. She liked him and it was easy to see why he and Dean got along. Benny was mild mannered despite his intimidating build, and he clearly loved the work as much as his green-eyed friend.

“Hey, Benny. You clean up well” she complemented him, taking in his crisp white shirt and black pants.

“Thanks, darlin’. My girlfriend, Andrea’s coming back from visiting family in Greece, so I’m headed to the airport” he told her, a big smile on his bearded face.

“Oh, wow!” she gasped. “That would’ve been amazing!”

“Yeah, she had a great time. I can’t wait to see her” Benny smiled, giddily. “Dean’s just bringing your car around.”

“Great” she breathed out. “Well, have a wonderful time with Andrea.”

“I will, and you know when things are more settled for ya, you should come over for dinner” Benny said, genuinely.

“I’d love that” she smiled.

“Take care, cher” he said, as he winked and walked away.

“Bye, Benny” she called out as she watched him leave through the front door.

Y/N watched through the windows as Benny waited to the side, as her car pulled up. She smiled as she watched Dean get out, wearing his aviators and blue and black plaid. Was there ever a time he wouldn’t look so damn breathtaking? The man was a walking sculpture. She watched as Benny walked off to his car, and Dean walked towards the front door. She smiled at him as he saw her and smirked, opened the door and took off his sunglasses. She looked amazing in her maroon A-line skirt and white top, with a fawn coat. Dean couldn’t help but admire her. She could wear a paper bag and still look stunning.

“Hey” he said, with the widest grin on his face. “Come on.”

He held out his hand and without a second thought, she clasped it with hers. Both of them had the same thought of how perfectly their hands fit together, but quickly pushed it aside. He led her outside and over to her car.

“Here she is” he said, dropping her hand, much to Y/N’s dismay. “Get in and turn the car on.” He tossed her the keys which she caught perfectly.

Y/N quickly got in the front seat and smiled, half excited and half nervous. She dropped her bag in the passenger seat, turned the key in the ignition, and heard it turn on. This time without any hideous sounds.

“Woooo!” he cheered with a laugh.

She laughed as she shook her head. He was crazy, but she loved how much he loved his work. She turned the car back off just as he came around to her side. She got out and automatically wrapped her arms around his neck, in a hug. He pulled her close, his arms around her waist, as he swayed them side to side. He chuckled, the rumble in his chest vibrating through her.

“Thank you so, so much, Dean” she whispered.

“No need to thank me, sweetheart” he whispered back.

The hug lasted a little longer than they had intended, and she quickly pulled away before they could overthink the gesture.

“I got to get home” she said, not really wanting to leave but knowing she had to.

“Yeah” he nodded, trying not to sound disappointed. “Come and find me if something happens, again, but you’re definitely good to go.”

“I’m sure I won’t have to” she said, as she sat back in her seat. Dean closed the door for her but leaned into the open window.

“See you around, sweetheart” he winked.

“Bye” she muttered, trying not to look flustered by his charm. _Cut it out, woman!_ She scolded herself as she pulled out of the garage parking, and turned her car in the direction of home.

* * *

Friday night quickly around again. Ben was staying at a friend’s house, which gave Dean the perfect opportunity to cook dinner for Lisa. With Styx _Renegade_ playing on the record player and the sauce for the lasanga simmering on the stove, he started mixing ingredients for dessert as the front door opened. Lisa walked in from having dropped Ben off and eyed him incredulously.

“What’re you doing?” she asked, leaning into the kitchen island.

“With the kid away for the night, I thought this was a good night to stay in and cook” he smirked, genuinely. “Have some alone time.”

She sighed heavily, shaking her head. “I can’t. I’m going out with the girls.”

He frowned, trying not to roll his eyes. “Can’t you go out with them some other time? I mean, you’re always out with them. I thought we could have a night to ourselves for once.”

“They’re my friends, Dean” she chastised him. “I don’t stop you from going out with your friends.”

She walked down the hall and into the bedroom, closing the door behind her.

An hour later, Lisa left the house with a slam of the door. Dean made up the lasanga and put it in the oven, but what was the point of eating it by himself? Now he didn’t even feel like eating it, wanting to order in pizza instead and threw back a few beers. As he started to dial the pizza place, he stopped. He looked up and out of the window in the kitchen. He smiled as an idea came to him.

Y/N was thankful for this Friday night to herself. She was going to call Katie and then watch a couple episodes of The Walking Dead which she had recorded, and get a pizza delivered. She made plans for Saturday to go watch a movie and have lunch with Charlie. She had asked for Meg’s number from Cas to invite her, but she was unfortunately working at the hospital. She promised to come to whatever the next thing would be, though, and Y/N was excited to meet her soon enough.

Just as she was about to sit down and call Katie, the doorbell rang a few times. Y/N frowned, wondering who could ring so urgently and hurried to the door. She swung it open and smiled as she saw Dean on the other side, looking flustered. The dark green shirt he was wearing was crumpled, and there was red and white checked dish cloth on his shoulder, which he probably hadn’t noticed.

“Please tell me you’re not doing anything tonight” he said, quickly, his hands rubbing over each other, nervously.

“Uh, no. I mean, I had a date with my DVR, but that’s about it” she said, shaking her head.

“Okay, well… if you want, I’d love to have you over to dinner. Ben’s at a friend’s for the night, Lisa couldn’t cancel her plans with friends when I asked her to stay for dinner, and I don’t want it to go to waste” he told her, a hopeful look on his face.

She smiled, not even thinking twice about it. “I’d love to.”

He pumped his fist, as he smiled wide. “You’re the best. Okay. In half an hour?”

“Absolutely” she nodded, his smile infectious as she found herself smiling too.

“Ah! Thank you!” he shouted happily, as he quickly leaned in and pecked her cheek. “See you soon!”

He quickly ran off back to his house, clearly not realizing what he just did.

Y/N shut the door, not being able to stop herself from smiling. She was trying to tread lightly but it was too hard. When he kept being the amazing human that he was, how could she? She knew she needed to call Katie as she got ready to go over there. She would set her straight.

She walked into her bedroom and opened up her closet, trying to figure what to wear. Considering the weather was starting to turn, a sweater and jeans would be most appropriate. She tossed the clothes on the bed and then stripped off, walking into her bathroom. She wanted to freshen up quickly after a long day at work. As she turned the shower on and then stepped in, she clipped her hair up to save it from the water. As she moved her body under the water, her mind wandered to Dean. She hated the idea of him trying to work things out with Lisa and her leaving him hanging. Did she care about him at all? Why stick around in a relationship that isn’t going anywhere? Did they even have their good days anymore? Having been in a bad relationship herself, she knew what it could do to your mind, and she hated to think that Dean was going through something awful by being in relationship that absolutely was not going anywhere.

She quickly lathered up, her mind still on Dean. These feelings of attraction weren’t new to her, but this was the first time they had been so intense. His face was somehow rugged and yet beautiful, his body was hard but his touch soft. Her eyes closed as her mind continued to wander, her hand moving down between her thighs. She rubbed her hand over her mound, the water cascading down on her only serving to make her wetter than she already was. Before she could continue, however, her mind quickly snapped out of the images of him. She moved her hand away, feeling guilty that she did what she did, but glad that she stopped before she went any further.

She turned off the shower and stepped out, wiping down. She quickly got dressed into what she was going to wear for dinner, and then dialled Katie’s number. She picked up on the second ring, her cheery voice on loudspeaker.

“Hey!”

“Hey, how are you?” she asked her friend.

“I’m great, but… you don’t sound so good” Katie replied, her voice full of concern for Y/N.

“Well, I’m about to head over to Dean’s for dinner. Just me and him” Y/N said, sighing.

“And you’re broken up about it because he’s still with his girlfriend? Right?” Katie asked, accurately assisting the situation.

“Bingo” Y/N replied.

She heard Katie breathe out deeply. “Y/N.”

“In my defence, he asked me because his girlfriend couldn’t cancel her plans with friends, and he didn’t want dinner to go to waste. I couldn’t say no” Y/N quickly explained.

There was a pause in conversation; Y/N knew that Katie was thinking.

“Look, there’s nothing wrong with going over there, as a friend and having a good time” Katie reassured her. “Just… be careful.”

I will” Y/N nodded. She glanced at the clock and saw that she should leave. “I should go.”

“Okay, keep me posted” Katie said.

“I will. Sorry we couldn’t talk for longer” Y/N apologized.

“It’s okay, we can make up for it soon” Katie said, simply.

“Definitely” Y/N agreed.

They said their goodbyes and hung up. Y/N quickly fixed her hair into more of a natural look, sweeping it off to the side. She put on her chocolate brown knee high heeled boots, sprayed some perfume on, and picked her phone as she left the house.

Y/N walked across the street, fidgeting with the neckline of her black sweater. She kept trying to pull it up over her shoulders, but the sleeves kept slipping down to rest almost off-shoulder. There was no point battling with it to do something it clearly couldn’t, so she left the neckline alone. Her Y/H/C hair was resting over shoulder, exposing the other. She had a split second of realizing that maybe she shouldn’t have worn it like that or the sweater, but it was too late now.

She walked up the porch steps and rang the doorbell. She was nervous to be alone with him, but she couldn’t help but feel a little excited too. It was alone time with Dean, and as much as she wanted it to be more, it was just two friends having dinner together. That’s it. It couldn’t be more. She wouldn’t let it be more. She waited patiently, but a breath caught in her throat when the door opened.

Dean had changed for dinner and was standing there in a dark grey Henley and dark blue jeans, looking like a freaking model. _Dear god, give me strength_ she thought as she smiled at him, admiring the way the Henley clung to his muscles.

“Hey, come on in” he smiled, letting her into the house.

He leaned down and wrapped his arms around her, pulling her into a hug. She smiled as her chin rested on his shoulder, and suddenly missed the closeness when he moved away.

As she walked in, Dean made quick work of checking her out. The black sweater she was wearing exposed her shoulders and collarbone, as her hair was styled in a simple yet perfect way. She was freaking stunning and he was regretting calling her over here.

 _Just keep it friendly and it’ll be good_ he told himself as he closed the door and walked into the kitchen.

“So, what can I get you drink?” he asked, as she followed him into the kitchen. “We got beer, wine, whiskey, a whole bunch of other spirits.”

She walked over to one of the high stools at the kitchen island, her heeled boots echoing through the house as they hit the hardwood floor and sat across from where he was standing.

“Wine would be great” she said, as she placed her phone in front of her on the counter, as she swayed a little to Zeppelin playing softly from the record player.

“Red or white?” he asked.

“Whatever’s going to go with dinner” she replied, with a small laugh.

“Red it is” he drummed his hands on the surface and then walked over to the other side of the kitchen, opening the glasses cabinet. He took out two wine glasses and selected a bottle from the wine rack on the bar he had next to the kitchen, before he walked back to his original spot.

“I didn’t take you for a wine guy” she teased, as she watched him pour a decent amount into each glass.

“I am when the occasion calls for it, and this definitely does” he said, as he passed one glass to her. He lifted his up in a toast and she did the same.

“To new friendships?” she suggested.

He smiled, nodding. “Absolutely.”

They clinked their glasses together and then both took a sip. She hummed as the liquid slipped down her throat.

“That’s amazing” she commented as she looked down at her glass.

“Yeah” he agreed as he picked up the bottle. “It’s pretty damn good and I’m not even much of a wine drinker.”

“So, how was work?” she asked, as she took another sip of wine.

His eyes lit up instantly. “Oh my god, today was freaking amazing! This guy brought in a beat up ’69 Camaro and wants us to restore it from the ground up!”

Her jaw dropped, just as excited as him now. “Oh my god, Dean! That’s incredible!”

He shook his head, his head still reeling. “I know, I swear as soon as he brought it into the back, me and Benny were losing our minds.”

“Wow” she laughed happily.

“It’s pretty much everything; new engine-” he started but suddenly stopped, clearing his throat. “Sorry, you probably don’t wanna hear this.”

She frowned, confused by the sudden change in his demeanor. “No, I do. Please, Dean, continue.”

“Oh, okay” he looked relieved as he went on. “So, yeah… new engine, tires, upholstery, paint job, the whole works.”

“That’s so awesome” she grinned.

“Yeah, and the guy’s pretty fucking loaded, too. So, he’s not sparing any expense. Paid in advance for everything” he told her, the smile never leaving his face.

“Dean” she sighed, her heart soaring. “This is seriously amazing. I’m so happy for you.”

“Thanks, Y/N” he half smiled, a twinge of sadness behind it. “I called and told Lisa as soon as he left. She said she was happy for me, but I know she’s not into this sorta thing, so…” he laughed it off, but Y/N knew he was hurting.

“Well, I don’t think you have to be in order to be happy for someone. I don’t know a damn thing about cars, but I’m really happy for you” she told him, sincerely.

“Yeah, I guess you’re right” he said, as he took a sip of wine. “I haven’t even told her about all my thoughts for expanding, either, because I know it’s not something she’s be interested in.”

“Expanding?” she asked, curiously.

“Yeah, I mean… we’ve had restoration jobs in the past, none as big as this one, but we’ve had a few. Every time we do, I keep thinking about opening another branch of the shop, specifically for restoration on classics, across town. Benny could run things here, while I’m at the new place for a while, and then we could just keep rotating between all of us at the shop. Maybe even hire a few more guys” he explained, a small grin on his face as he did.

“Dean… I think that’s brilliant. Not to mention incredibly different. That could really put you on the map” she complemented his plan, loving the idea instantly.

“Yeah” he nodded. “We’re flying already, and I’m really happy with where we are, but I know that we’d be unstoppable if that happened. You know?”

Y/N smiled; she loved seeing how ambitious he was. She couldn’t help but feel bad that he probably hadn’t shared this with anyone, except for maybe Benny.

“So, what about you? How’s work?” he asked, changing the subject to her.

“It’s good. I feel like I’m finally settled into the job, it happened quicker than I thought it would. I feel like Cas and Charlie had something to do with that. They’ve been so supportive of me” she replied, slowly turning her glass by the stem.

“Yeah, they’re awesome” Dean chuckled, incredibly matter of fact.

“We’re moving into teaching _To Kill A Mockingbird_ next week, which I’m excited about” she smiled; it was one of her favorites.

“Man, I wish I had teachers as excited as you about school. Maybe I would’ve enjoyed it too” he laughed as he recalled his school days.

“Not a school guy, Dean?” she teased.

“God, no. I mean, I graduated, but that’s about it. I just didn’t have it in me like Sammy did, you know?” he said, truthfully.

“Well…” she said, as she laid her hand on his. “I don’t think there’s anything wrong with that. What you do matters, too. Not everyone can have the skills you have.”

Dean had the sudden realization that her hand felt incredible in his and he never wanted her to let go. She really cared about him and what he did, and that made his heart beat just a bit faster, knowing that.

“So, no hare-brained ideas like me?” he chuckled, but his self-deprecating humor wasn’t lost on her.

“Well, firstly, your idea isn’t hare-brained” she quickly chastised him for the way he was thinking. “And secondly, no big plans other than eventually moving into high school. Teaching Literature; that’s where I want to be.”

He nodded, all while trying to keep his naughty teacher fantasies at bay. “That’s great.”

“I mean, don’t get me wrong I do enjoy teaching the younger kids, but they’re a handful. Having more of chance to teach the stuff I really love in high school… it would be amazing” she said, her eyes dreamy and hopeful.

“Well, I hope you get there. Those kids are gonna have one badass teacher” he smirked as he complemented her.

“Thanks” she felt the heat rise in her cheeks. “I hope so, too. I’m dying to get the chance to teach my favorites; especially Jane Eyre.”

“That had something about a fire, right?” he asked, trying to recall if he knew anything about that book.

“Yeah. I absolutely love it” she sighed.

“Hey, what do you know, I know something” he laughed.

She shook her head, smiling as she gestured to the bookshelves in the living room. “Seems like you know plenty.”

“Those are mostly Lisa’s” he waved her off.

“Really?” she asked, an eyebrow raised. She hopped off the stool at the kitchen island and walked over to the shelves. She scanned them quickly, and took out a book, holding it up to him. It was _Slaughterhouse Five_. “Somehow I don’t think Lisa’s a Vonnegut fan.”

“I guess not” he said, as he walked over, slowly.

“Or Dracula” she said, picking that one up after putting away the other.

“Yeah, I… um, I like the sci-fi, and horror stuff” he shrugged.

“I do too” she smiled.

He returned it, finding their conversation so easy it scared him. It shouldn’t have been that simple with someone he couldn’t be with.

“Food shouldn’t be too hot now” he said, breaking the moment between them. “Let’s eat.”

Dean walked back into the kitchen and picked up the dish that was cooling down from the corner near the stove. He brought it over to the table and sat down at the head of the table, just as Y/N brought her wine glass and Dean’s over. She sat down at the corner where the place setting was as he lifted the lid off the dish. The smell was absolutely divine as it reached her nose. Dean cut into the lasagna and placed the piece on her plate with a slice of garlic bread and some salad. She smiled as he passed it to her and took out his own serving, minus the salad. She had to laugh.

“Alright, go ahead and give me the verdict” he said, wanting her to eat first.

She dug in and took a forkful, bringing it to her mouth. As she chewed, her eyes closed, a smile gracing her face.

She opened her eyes and looked at him. “That… is incredible.”

“Glad to hear to that” he smirked as he dug in.

“So…” she swallowed her mouthful before continuing. “Who taught you how to cook?”

“My mom, as cliché as that sounds. She didn’t want me eating take-out all the time when I moved out years ago, so she taught me a few things” he told her.

She nodded, smiling. She couldn’t help but think about how she found guys who cooked incredibly sexy.

“Are you and your mom close?” she asked.

“Yeah, we are. I was the one who was there for her when she and dad had a big fight. We started to talk more often after that” he replied, taking another bite.

“What happened?” she asked, softly. “If you don’t mind me asking…”

If it was anyone else, he probably would’ve shot the question down, but he was comfortable around Y/N. He felt like he could tell her things and she wouldn’t judge anyone. Even Lisa barely knew anything about his family.

“I was around 23, 24 and working with dad full-time by then. Sammy was at college. Things weren’t going great with the business; we were losing money and he was getting really stressed. He was forgetting things, just trying to provide and he forgot their anniversary. She got really upset and found out just how bad things were. There was a lot of yelling, she cried a lot. One night, he just left. He came back after a month, apologized a lot to her, and she forgave him. He was really different when he came back; a better version of himself. Things have been really good ever since” he explained, that memory still hard to think about.

“Do you guys know where he went?” she asked, her eyebrows furrowed.

“Yeah, he went to a family friend in South Dakota. He helped turn things around for the business too, he’s a mechanic as well” Dean replied, smiling as he thought about his “uncle”. “Dad told me later he was just ashamed and didn’t know how to face her after what happened. He felt like he couldn’t provide for her, that she deserved better. He’s always felt like he didn’t deserve her, and she’s always felt like he’s exactly the person she was meant to be with.”

“I’m glad everything worked out” she smiled but frowned when something occurred to her. “Did he ever apologize to you?”

“He didn’t need to, I understood what happened and I never judged him for it” he shrugged.

“Well, that maybe so, but it put a pressure on you that you didn’t need” she said, understanding the situation completely. “I’m just saying, it’s never too late for that conversation.”

A silence fell as Dean thought about what she just said. About how she just understood, so instantly, so clearly. He cleared his throat as he continued to eat, his mind flooded with a million thoughts about her.

“You know a lot about my family, so I gotta know something about yours now” he said, wagging his eyebrows as he looked at her.

She laughed as she racked her brain for something interesting. “I wish I had some interesting stories, but I don’t.”

“Well, who are _you_ closer with?” he asked.

She chewed quickly as she put her fork down. “Dad. I mean, I love my mom and we get a long great, but she can be a little too assertive sometimes. Whereas, my dad always knew how to get her to calm down and let me take the reins when I needed to. He always let me make my own choices, and if I ever made a decision that didn’t turn out well, he’d tell me that it was okay. It was a learning curve and that I would do it differently next time.”

Dean nodded, approvingly. “Smart.”

“Yeah” she smiled sadly, her heart longing for her family. “I miss them.”

“That’s another thing I gotta ask…” Dean started as she looked at him. “You’ve said you’re close with them since I first met you, so… why did you move so far away from them?”

There it was. The question she had been dreading. Yes, she had already told Charlie but that came up organically, through their conversation at the bar. Telling him was different.

Dean sensed a shift in Y/N and knew something was wrong. Her hands closed up, she avoided looking at him as she stared down at her plate and looked like she was shaking. He had never seen her like this, and he was scared that he had really upset her.

“Y/N, are you okay?” he asked, concerned.

“Yeah, I just… don’t know how to tell you” she replied, as she picked up her glass and took a big gulp of wine.

“Hey, you don’t have to tell me anything, it’s totally fine. I’m an idiot, I shouldn’t have brought it up” he apologized but she shook her head, causing him to stop.

“No, you’re not. It’s okay” she said, quietly. “I want to tell you. You’ve told me so much about your life, it’s only right I tell you about mine. Plus, I’ve talked about it with Charlie, so I’ll be okay.”

“Y/N, you don’t have to just because Charlie-” he said but she cut him off again.

“It’s okay, Dean. Really” she let one side of her mouth turn up, letting him know it was fine.

When Dean just looked at her intently and didn’t say anything, she decided that for now she’d tell him what she could. It wasn’t that she didn’t trust him, because she did. Completely. She just needed to hold some of it back for now. She told Charlie everything because somehow it was easier to open up to her. Dean was someone she was starting to have genuine feelings for, even though she shouldn’t be. As much as she wanted to open her whole heart to him, he wasn’t hers to do that.

Y/N cleared her throat from the roughness that built up because of the alcohol and her emotions already affecting her.

“I was in a relationship for a year and a half. His name was Ethan. He was a friend of a friend and we met at that friend’s birthday party. He was charming and funny, a little arrogant but I didn’t think much of it at the start. We started dating and he generous, but it didn’t last long. He was incredibly controlling, telling what I should or shouldn’t do. Everyone would tell me that wasn’t normal, and deep down I knew that, but he was just so convincing that I thought that he was trying to make me better” she told him, her voice shaking.

Dean continued to look at her, slipping his hand over hers. Y/N felt the heat of his hand on hers as she turned hers, locking them together.

“It took a night of a lot yelling, of finally realizing what kind of a man he was, to make me finally leave him.” She shook her head, closing her eyes as the waves of the past began to flood in.

She felt Dean’s hand squeeze hers, reassuring her that she was okay. That she wasn’t in that place anymore. It was a year later, but the effects of what Ethan had said, what he had done, still lingered, still held onto the rope that was nearly broken. Most of the strands were frayed and lost, but the last strands still needed to be torn.

Y/N opened her eyes and looked at Dean. She saw his eyes, sad but fiery, as he shook his head. She had probably scared him off and she didn’t blame him, honestly.

“Y/N, you’re… you’re the strongest person I know.” Dean gripped her hand, stroking his thumb across her knuckles. “You’re amazing. Beautiful. I-, fuck I wanna hurt him for what he did to you.”

Y/N huffed as what she was feeling got the better of her. “Fortunately, he’s far enough away that you don’t have to.”

“Is your family safe with him around?” he asked, concerned.

“Yeah, they are” she nodded, wiping under her eyes. “He uh… he was around for a while, I’d see him a lot, but he eventually moved out to L.A. with his girlfriend.”

“Good riddance” he grumbled, under his breath.

“I knew he was gone but still being there… it just became too much. I was in therapy for a year just trying work through everything. When I saw this job come up, I jumped on it straight away. I miss everyone back home, but I knew I had to leave” she explained, blinking a few times to keep the tears at bay. “There’s a lot more to it, but… I just…”

Dean shook his head as he leaned forward, his eyes boring into hers. “You don’t have to tell me more, Y/N.”

She couldn’t help but smile as she looked at him. “Thank you. For listening. It’s not everything but I wanted to tell you.”

“Well, thank you for telling me what you could. I can’t imagine how hard that was.” He gave her a soft smile, as he looked down at their hands. Still joined together.

“It was, but…” she contemplated whether she should say what she was about to, but it was the truth and she wanted him to know. “I trust you.”

Dean nodded, realizing that it meant a lot for her to do that. The fact that he had earned her trust in a short amount of time was something he wasn’t expecting. Now that he had it though, he made a promise then and there to himself that he would never let her doubt him.

“I trust you, too” he spoke softly, but he smiled when he saw the corners of her mouth turn up and he knew that she had heard him.

Y/N was glad to know that she had Dean’s trust too. It took a lot for a person to tell someone about their family issues, and the fact that he did just meant that he was comfortable around her. She was grateful for that and if he felt like that with her, then she certainly did with him, allowing her to tell him about her past. Even if there still a bit more to the story.

The conversation turned lighter after that. They discretely unclasped their hands from each other, as they continued to eat. They both hid the fact that they missed the feeling. They asked each other about their favorite things, the conversation moving quickly between movies, books and music. They both decided that Zeppelin was the shit, and no one could tell them otherwise. Dean quickly got up and changed the record to another Zeppelin album, and sat back down.

“Okay, don’t judge me” she said, looking sheepish as she pointed to the record player. “I still don’t have this album.”

“What?” he asked as he leaned forward, eyes wide. “You’re kidding.”

“No, unfortunately. I’m pretty sure dad just never got around to buying it, ever” she told him, frowning.

“Well, we gotta change that soon” he shook his head but with a small smile.

Y/N sat back in her chair; her plate now empty. That had been one of the best meals she had had a long time.

“Damn, that was incredible” she said. “Thank you.”

Dean smirked as he started clearing the plates and cutlery. “No problem, sweetheart. I’m glad it wasn’t failure.”

“Somehow I don’t think you could fail at this” she laughed slightly, as she stood up and helped him.

“Hey, I got this” he groaned as he nudged her, silently telling her to stop helping him.

“No way, you’re getting help whether you want it or not” she said, as she followed him into the kitchen.

He started washing up as she grabbed a cloth and started wiping whatever he washed.

“That was my job when me and Sam would clear up” he gestured to her, as she stood there with the towel.

“Really?” she asked, raising an eyebrow. “You weren’t the one washing?”

“Nope, Sammy didn’t trust me not to splash him” he laughed.

She joined in. “Brothers.”

“Eh, I’ve done worse” he shrugged, passing her a plate.

“Like what?” she wondered.

“Let’s see…” a wicked grin graced his face. “Itching powder in his boxers, Nair in his shampoo…”

She let out a loud screech. “Oh my god, no!”

“Yeah, I got into a lot of trouble for that one” he laughed, sheepishly.

“Good” she said, playfully elbowing him, but a little hard.

“Ow!” he moaned as he laughed. He turned the water off and wiped his hands on another cloth.

“Did you and your sister ever prank each other?” he asked.

“Uh, less purposely pranking and more just getting each other back for something” she recalled. “She’s older so she always felt like she deserved the most time in the bathroom. She spat in my hair while we were brushing our teeth and I bent down before her. So… I shaved off one of her eyebrows while she was sleeping.”

Dean threw his head and laughed loudly. “Wow, didn’t expect that, Y/L/N.”

She laughed as she wiped down the last of the cutlery. “Luckily, we grew out of all of that pretty quick.”

Dean smiled. She always wore a far off look on her face when she talked about her family. It must’ve been hard to not see them every day. He couldn’t imagine doing that. He went over to the oven and opened it, taking out a tray with two white ramekins. Y/N gasped as she walked over.

“You… you made chocolate molten cakes?” she asked, staring at them before looking up at him, wide eyed.

“Yeah” he said, nonchalantly. “There wasn’t enough time for pie, so chocolate cake it is.”

“You’re… full of surprises, Dean Winchester” she shook her head. He wasn’t real. He couldn’t be.

“More wine?” he asked, as he waited for the ramekins to cool.

“Oh gosh, I’ve had three glasses. I really shouldn’t” she said, looking at the bottle. “Ah, screw it. Sure!”

Dean chuckled and poured some for Y/N and then himself as _What Is and What Should Never Be_ began to play.

_And if I say to you tomorrow_

_Take my hand, child come with me_

_It’s to a castle I will take you_

_Where what’s to be, they say will be_

He watched as she hopped up on the kitchen bench and took her glass. He took out a spoon from the drawer and slowly cut into the cake, watching the melted chocolate ooze out. He took some in the spoon and brought it over to her. He blew on it slightly, as he held his hand under it.

“Okay, tell me if it’s good” he said, as she leaned in and took the mouthful in.

The sound she made as she closed her eyes caused the heat to rise in his cheeks.

“Fuck” she moaned, delightedly. “That’s so fucking amazing!”

He sighed in relief and cleared his throat at the sounds she made, as he grinned at her. “Good to know.”

“You are an incredible cook, Dean. I’m glad I came over tonight” she said, looking at him as he took a bite himself.

_Catch the wind, see us spin_

_Sail away leave today_

_Way up high, in the sky, hey_

He hummed as he tasted it himself. “Well, me too. All this didn’t go to waste, which it definitely would’ve considering Lisa couldn’t stay, so thank you.”

“You’re welcome” she smiled, as she took a sip of wine.

He saw a speck of melted chocolate on the side of her lips and lifted his hand.

_But the wind won’t blow_

_You really shouldn’t go_

_It only goes to show_

“Hey, you got a little chocolate… right there” he murmured as he swiped his thumb across her lips and removed it.

“Oh” she gasped. “Thanks.”

The song continued to play as they looked at each other, their faces close as their eyes met.

_That you will be mine_

_By taking our time, ooh_

Before he could think twice about it, Dean leaned in and pressed his lips to hers. It took her a second, but quickly her lips moved against his. The kiss became heated instantly, their lips moving together sensually. He moved forward between her legs and wrapped his arms around her waist, as her arms went around his neck at the same time her legs wrapped around his hips. Her fingers combed through his hair, her fists tightening in the short spikes as he softly bit her bottom lip. She moaned into the kiss as his hands pulled her in, trying to get as close to her as possible.

_And if you say to me tomorrow_

_Oh what fun it all would be_

_Then what’s to stop us, pretty baby_

_But what is and what should never be_

Dean’s lips left hers as they trailed down, nipping at her jaw and moving down further. He nipped at her neck, causing another moan to leave her as he found her weak spot. She brought him in closer, gripping the short hair at the back of his head, tight. He slowly slipped his hand under her loose sweater, the heat of his hand meeting her back and spreading through her body. When his hand travelled up her back, the spell she was under broke.

Y/N pulled away from Dean, looking up into his green eyes. They were dark and blown wide from the moment of weakness they both just had, and she was sure hers were the same. She pushed herself away from him, her legs falling away from as he moved out of her space.

“I can’t do this” she said, frantically shaking her head.

She quickly hopped off the bench, looking for her phone. It was still on the island where she had left it. She quickly picked it up and ran towards the door.

Dean snapped out of his trance and followed behind her. “Y/N, wait!”

She didn’t hear him as she swung the door open and raced out, bounding down the stairs as she ran across the street.

Dean watched from the threshold as she ran into her house, shutting the door behind her. He thought that he should go over there, but knew it wasn’t a good idea. He stepped back in and closed the door. He ran his hands through his hair, messing up the spikes and ran them back down his face. He walked back into the kitchen, replaying what just happened over and over in his head. He had lost control and the guilt was beginning to settle in. Lisa didn’t deserve that, no matter how bad things were between them. He shouldn’t have done that with Y/N, she didn’t need this.

As he ran his hand over his lips, however, he closed his eyes. He could still her lips, still feel her touch on his body, still feel the smoothness of her skin against his hands. In that moment, it felt so right to be in her arms. It hadn’t felt wrong.

He knew now that he had just complicated things even more. Every fibre within him wanted to be close to her again, but he couldn’t.

He just had to try even harder now, with Lisa. That was the only way to not think about Y/N anymore.

That was the only way to fix things.

* * *

Y/N slammed the door behind her as she entered her house. She breathed heavily, her frantic run from Dean’s had winded her. She walked into the kitchen and opened the tap at the sink, flicking specks of water at her face. She took out a glass and filled it, gulping the water down.

Once she had calmed down slightly, her mind wandered back to what happened. She had kissed Dean. Dean, who was in a relationship. Dean, who was practically a father to a student in her class. Dean, who made her laugh and let her tell her story, without judging her. Dean, who said she was strong. Dean, who told her she was beautiful. Dean, who made her feel safe. Dean, who she was starting to have real feelings for.

It felt right to be with him, when it should’ve felt wrong. She was a horrible person and she never should’ve gone over there tonight.

She couldn’t see him again. Yes, it would be hard considering their close proximity, but she couldn’t. She had to forget about how she felt and remember he had a family. A family that didn’t deserve this, even if things were rocky.

She had to let go of Dean, when every instinct was telling her to pull him in and hold him tight.

She had to let him go, no matter how much it hurt.

She had to let him go, because it was the right thing to do.

**Notes for the Chapter:**

> So... What did you guys think? lol
> 
> Please leave kudos or comment, I'd love to hear your thoughts! :)


	6. A Lesson in Starting Fresh

**Summary for the Chapter:**

> Y/N and Dean try to distract themselves from what happened the night before, despite the fact that they can’t stop thinking about each other. However, after an incident at school between Ben and another student, Y/N makes a difficult decision. Later, as she meets someone who could help her forget about Dean, he finds out what Lisa’s been hiding from him.

**Notes for the Chapter:**

> Halfway through! Hope everyone is liking it so far! :)
> 
> Warnings: Angst, Guilt, Alcohol consumption, Some fluff, Mentions of cheating.

* * *

The next morning brought cloudy skies, a gloom that matched the way Y/N was feeling as her eyes fluttered open. She turned her head and looked out the window, frowning as she saw the clouds in the sky. She loved the summer but now with fall settling in, the hopes for even one more day of warmth were over.

The thoughts of Dean hadn’t left her mind since the night before, as much as she tried to not think about him. The way he felt against her, his hard torso against hers, his calloused hands against her skin, the feeling of his muscles against her hands even through his shirt, his lips against hers… it had all stirred feelings within her that she wished she didn’t have for someone who was taken. She couldn’t do anything about the way she was feeling.

As she stood up from the bed and rubbed the sleep out of her eyes, she couldn’t help but think about how much more complicated things had gotten. All because she couldn’t keep away from Dean.

She really was in trouble.

* * *

The shower turned on, wetting Dean’s hair as he tilted his head into the spray. The water flowed down his back, seeping into his skin. He closed his eyes and stroked the water through his hair a few times to get it soaked down to the scalp. He opened his eyes and stared at the tiled wall in front of him. He couldn’t stop thinking about what happened last night. The way Y/N felt against him, her smooth skin against his calloused fingers, her soft lips kissing his. He couldn’t get her out of his mind; being that close to her turning him on in ways he hadn’t been in a long time.

As Dean finished up in the shower and got dressed for the day, his mind was still on Y/N. However, guilt washed over him. He felt like he needed another shower. Maybe ten. It had been quite a few months since he and Lisa had been intimate in any way. The last time they even tried to start something up, she stopped him before anything could happen, saying she had lost the urge. He knew there were other ways to be close to someone but having been in a relationship for 3 years, and suddenly lacking a sex life in the last few months meant that he was incredibly frustrated. It had been a lot of time with his hand, in the shower or the bedroom when no one was around. He had never strayed however, and he wouldn’t, even if he had a moment of weakness with Y/N. He had stopped himself and he was going to make an effort with Lisa. Then maybe, just maybe, they could go back to the way things were.

Dean walked into the kitchen, seeing her and Ben laughing about some video on her phone, as they ate breakfast. He smiled as he saw her face light up. She was a beautiful woman, and anyone could see that. He cared very deeply for her, always had. It just never became more than that. He loved her but he wasn’t in love with her, but if they tried again, he knew that he could be.

He walked over and watched her lift her head to see him walking towards her. He leaned in and kissed her slowly on the lips, trying to see what her reaction would be. When she pulled away with a small smile, he tried not to feel too optimistic.

“Looks good” he said, as he sat down and piled several pieces of bacon onto his plate.

“It’s probably going to rain, so we can’t go to the park and swing a few bats” Ben informed him, sadly.

“Damn” Dean muttered as he looked out the windows and saw the grey skies. “That’s a shame.”

“I have to run a few errands, so you’re both welcome to join me” Lisa chimed in.

Ben groaned as he pushed the eggs around in his plate.

Dean snickered as he watched him. “Maybe I can call Sam. He’s not working on a case right now; we can drive into the city and all hang out at the big arcade. How ‘bout that?”

Ben’s eyes lit up. “Really?”

“Yeah, if it’s cool with your mom” Dean said, looking between him and Lisa.

“Sure” she smiled at her son.

“Yes!” Ben pumped his fist, eating his food properly now.

“Thanks” Lisa said as she looked at Dean, with half a smile.

Dean nodded as he tucked in.

It wasn’t much of a reaction, but he would take what little happiness he could get from her.

* * *

“Alright, go nuts” Dean told Ben, and watched the kid dash off into the arcade.

Dean turned to Sam and shook his head with a laugh, taking a sip from his beer. They both sat in the adjoining diner, watching Ben through the windows. While he was going crazy on all the games, Dean got the chance to talk his brother.

“How’s Eileen?” Dean asked, his fingers drumming against the bottle to the beat of the AC/DC song playing overhead.

“She’s good, a little tired, but good” Sam replied, taking a bite of his salad. “The new firm’s kicking her ass but she’s kicking theirs right back, so I’m proud of her.”

Dean smiled, albeit a little sadly as he saw how much his brother loved his wife. “That’s great, man.”

There was a moment of quiet as Dean kept picking at the label on the beer bottle, when Sam spoke up.

“I don’t know if I should ask this, but… how are things with Lisa?” Sam asked, tentatively.

Dean huffed, shaking his head. “Pretty much the same as always. If we’re not ignoring each other, we’re fighting about something. I’m trying to be a little more… I’m trying to get us back to some place closer to how we were but… I don’t know.”

Sam frowned, lines forming on his forehead as he worried over what Dean just said. “You’re sure you don’t want to just… end it before things get worse?”

“No” Dean said, too quickly. He looked out the window to see Ben playing Galaga. “I can’t do that to him.”

“Dean, what you and Lisa are doing is worse for him. This way, at least it’s a clean enough break and everyone can move on without too much damage” Sam explained, pushing his plate to the end of the table, finished with his meal.

“I know” Dean said, quietly.

“So, what’s the problem?” Sam shrugged. “Yeah okay, you had some good years, and that’s great but… you can try all you want to get those years back, it might not do anything. Lisa has been emotionally checked out from this for a long time now, and let’s face it, you are too. You’re both just in this for Ben.”

Dean took a swig of his beer but didn’t say anything.

“Dean, you deserve to be happy with the right woman, not miserable with the one who you _thought_ was the right one” Sam said, leaning his arms on the table as he looked his brother.

“Sam” Dean groaned. “Just stop, okay?”

“But, Dean-” Sam started but Dean cut him off.

“You said what you had to say, alright? You made your point. Let’s move on” Dean said, his tone almost pleading.

“Okay” Sam whispered.

“Good” Dean muttered, picking up a few fries from his plate and shoving them into his mouth.

With his brother’s mind preoccupied with the food in front of him, Sam stared at Dean, seeing the turmoil written on his face. His brother was loyal to a fault, but he had seen for a while now how much this relationship was hurting him. He never listened to anyone, not him, their parents, his friends, about breaking up with Lisa. He always cited that Ben was the reason he needed to stay, but there was also another reason that Dean hated to admit to anyone, even himself. Sam could see it, though. His big brother was afraid of being alone.

Sam knew he couldn’t tell Dean to break up with Lisa any more than he already had. He had to realize that’s what he needed for himself, and maybe, he could find peace after it.

* * *

Later in the evening, Y/N laughed as she opened her door and walked into the house, Charlie following in behind her. They had just come back from a slasher movie, which hadn’t turned out to be very good, but you couldn’t expect a lot from a B grade film. That didn’t matter though, as they still got to enjoy lunch before that, and were just going to hang out now that they were at Y/N’s.

“God, that guy couldn’t act!” Charlie complained as she sank into Y/N’s couch. She kicked her converse off and brought her legs up. She had instantly made herself comfortable at her house, and Y/N couldn’t be happier with that.

Y/N continued to laugh, nodding as she agreed. “I know! And what about the scene where the axe went through his head? It totally didn’t connect!”

“Right?” Charlie shook her head, giggling.

“Alright, what are we drinking?” Y/N asked as her laughter died down and she walked into the kitchen.

“Whiskey” Charlie replied, quickly without thinking too much about it.

“Ooh, yes. Perfect for this weather” Y/N said, as she looked out the window at the light drizzle.

Y/N brought the bottle and two tumblers over, sitting next to her redheaded friend. She poured a couple of fingers in each and handed her one, clinking their glasses together. They both took a sip and Y/N sat back, smiling contently. It had been a good day, a nice distraction from her neighbor who she had feelings for. Her face must’ve changed when she thought about him for split second, because Charlie picked up on it.

“You okay?” she asked, curiously.

“Yeah” Y/N huffed with a small laugh. “Why wouldn’t I be?”

“You just seem like something’s on your mind” Charlie shrugged.

Y/N looked away from her and sighed. She was going to flip when she told her.

“I… went over to Dean’s for dinner last night” she started, waiting to get to the point.

“Nice. I hope Lisa was a bit more open than last time” Charlie commented.

Y/N bit her lip nervously, before letting it go. “She… she wasn’t there.”

One of Charlie’s eyebrows lifted up. “Okay…”

“We, uh… we had a great time. We talked a lot about his family, about mine. I… I told him about Ethan” Y/N told her, staring into her glass at the amber liquid.

“Wow” Charlie breathed out. “How did that go?”

Y/N smiled as she thought back to how he told her she was the strongest person he knew. She didn’t feel like she was, but just knowing that he thought that about her made her feel like she could be.

“It went well. In the moment I thought about against telling him, but he just… he made me feel so safe that I told him a little of it” Y/N said, the soft smile still on her face. “Not everything just yet, but I trust him and maybe I can tell him more, eventually.”

Charlie stared at her, knowing her new friend was falling for one of her old friends was incredible to see, but she didn’t want her heart to get broken by the situation at hand.

“Y/N… I’m glad you felt the confidence to tell him. I’m even more happy that he made you feel safe to open up, but… but you have to tread lightly here” Charlie said, carefully.

“I know” Y/N agreed.

“It’s my fault, really. I told you about Dean and Lisa’s relationship, but that was only because of what you said happened at dinner here-” Charlie said, but cut her off.

“It’s okay, Charlie, really” she reassured her, taking her hand in hers. “I know why you told me that. Believe me, I know. It’s just…”

“What?” Charlie knew there was something she wasn’t telling her.

Y/N sighed in defeat. “We kissed.”

“What?!” Charlie yelled, sitting forward as she stared wide eyed at Y/N.

“We had a great time, we were laughing, and he made dessert, and… fuck, it just happened” Y/N shook her head, saying it out loud made it more real, and made the guilt flood in again.

“Y/N!” Charlie yelled.

“I know!” Y/N yelled, burying her face into the couch cushions. “I’m a shitty person.”

“No, you’re not” Charlie told her, helping her off the couch cushions. “We just can’t let that happen again.”

“And I won’t” Y/N vowed. “I think it’s out of my system in the crappiest way possible, and it’s done now. Even if it was the best kiss of my life… I’m done.”

“Really?” Charlie asked, in awe of the statement she just made. “The best of your life?”

Y/N nodded, sheepishly. “It was like… like I was always meant to be there, with him.”

A silence fell as the two friends looked at each other, before Charlie spoke.

“I hate to say it, but… I think that’s where it has to end” Charlie said, as gently as she could.

“I know” Y/N nodded, firmly.

On those final words, the friends moved away from talking about it. Y/N knew that what happened last night couldn’t happen again. It would be hard to let him go, but she had to. She wasn’t going to break up a family. That’s not the kind of person she was. She had a moment of giving in, but it was done and dusted. Swept under a rug, never to see the light of day again. From that point forward, it would be strictly professional. She was Ben’s teacher and that was it. She may be their friendly neighbor, but she couldn’t be Dean’s friend.

She couldn’t have another moment to give into.

* * *

Dean smiled as he sipped his beer while sitting on the couch, watching Ben recall the day’s events to his mom. They had a great time with Sam at the arcade, playing all the games and eating junk food. After a while, Ben retreated to his room and Dean knew he’d been listening to his music before going to bed.

Dean walked into the bedroom after finishing his beer, watching Lisa get changed into her pyjamas. He moved up behind her after she took her top off, wrapping his arms around her waist. He leaned down, placing kisses along her shoulder.

“Dean” she said, a slight laugh bubbling up from her. “Stop.”

“Oh, come on, Lis. Ben’s in his room, probably has his headphones on” he said, between planting kisses on her shoulder. “We haven’t in a while…”

“Dean, please” she said, as she pulled away from him. However, when she turned around, she looked a little annoyed. “Maybe… maybe another time.”

Dean was surprised by that, considering she laughed a little when he came up behind her. “Yeah. Okay.”

She moved away from him, walked into the bathroom and shut the door, locking it.

Dean sighed as he changed into a pair of sweatpants and a black t-shirt. He left the room and into the living room, turning the lights off. He dropped his phone on the coffee table and laid down on the couch. It was a familiar feeling as he had done this a few times over the last year. Considering things didn’t go the way he thought they would tonight, he knew it was better to stay away for now. He pulled the throw blanket over himself and closed his eyes.

After some time, he opened them. He wasn’t going to sleep. He lifted his head and looked at the clock on the wall, the time reading 10.30pm. It wasn’t late for him, as he usually fell asleep in the AM on a weekend. He picked up his phone and started scrolling through different things, before an idea came to him. Hopefully she wasn’t asleep yet.

Y/N sat up in bed, reading, the bedside lamp provided the light she needed as it bathed the room in a warm glow. She pushed her red glasses up the bridge of her nose when she felt them falling, flipping the page. Charlie had left an hour ago, which gave her some time to herself and the ability to lose herself in her latest read. As she read, her phone chimed. She frowned, wondering who could be texting her at this hour. She thought it must be Charlie, wanting to tell her some funny anecdote, but her eyebrows furrowed as she picked up her phone from the bedside table and looked at the screen.

**Dean:** _Any chance you’re free tomorrow? We need to talk._

She sighed as she placed her book down next to her and typed out her response.

Dean frowned as he saw what she had written.

**Y/N:** _I don’t think that’s such a good idea, Dean._

**Dean:** _We can’t just ignore what happened, Y/N._

She shook her head. She couldn’t be pulled into this again. She had no desire to talk about it, choosing instead to forget about it and make sure it never happened again.

**Y/N:** _I think that’s exactly what we need to do. Forget it happened. Goodnight, Dean._

Dean looked down at the message and shook his head. How could he forget when she was constantly on his mind? He was trying, had been trying all day, but the fact was he couldn’t stop thinking about her. He couldn’t deny he had developed feelings for her. He told himself he would try with Lisa, but would it do any good? He just needed to talk to Y/N and see whether they were on the same page or capable of getting there, and then go from there.

He decided to put his phone and sleep on it. Maybe things would be clearer in the morning.

* * *

Monday quickly rolled around, and Y/N was thankful. School was a good distraction from the drama in her life, even if Ben was there. She was going to have her 8th graders after lunch, so as she ate, she had enough time to look over what she needed to do for class. She was in the middle of reviewing her lesson plans when she heard someone call out her name. She looked up and saw Chuck walking towards her.

“Hey, Y/N, can we talk for a minute?” he asked, politely.

“Sure” she replied, but slightly nervous as she didn’t know what this is about.

As she followed him into his office, she sat down across him as he sat at his desk.

“Don’t worry, it’s not anything to worry about” he assured her, when he saw her looking like a deer in headlights. “I just wanted to ask you how things have been going.”

She sighed in relief, a smile appearing on her face. “Things have been great. Challenging, but I think I’ve handled it.”

“That’s great to hear” he returned her smile. “I’ve had some calls from parents telling me how much their kids have liked you, so all I can say is keep doing what you’re doing.”

“Thanks, Mr. Shurley” she said.

“Ah” he waved a finger at her.

“Sorry” she laughed, slightly. “Chuck.”

“You’re welcome” he said with a small nod.

She quickly left his office with a smile on her face. Hearing that from Chuck was exactly what she needed today. It was the reassurance she needed that coming to Lawrence was a good decision. It was a reminder of why she came here, for this job and to inspire these kids, not for any unnecessary situations outside of school. She really just had to put her head down and do what she needed to and forget about Dean. Even if he did live across street from her, right now, he couldn’t exist.

As she walked from the staff room to the classroom after lunch, she watched kids file into the rooms, ready for the next period. She smiled as she turned the corner, ready to see her students but it dropped the minute she entered the room.

Ben and another student, Tommy, were roughly pushing each other back and forth, some of the other kids in class yelling for them to stop, while others yelled for them to keep going. She quickly dropped her things on the desk and rushed over, attempting to pull them apart.

“Stop it, stop it right now” she said, her teacher voice louder than usual. “Ben, Tommy – STOP!”

She got in the middle, either hand on the boys’ shoulders, watching them breathe heavily as they glared at each other. She thought about sending them over to Chuck’s office, but they’d probably kill each other on the way over.

“You two, sit down right now. We’re going to Mr. Shurley’s office straight after class” she said, sternly.

The rest of the kids were timid for the rest of the class. She had rearranged some of them so that Ben and Tommy were sitting as far away from each other as possible. Things were tense through the whole period, but she was glad that once it was over, Ben and Tommy stayed in their seats as the other kids filed out.

“So, who wants to tell me what happened before we head over to Mr. Shurley’s office?” she asked, looking between both of the boys.

Tommy stared down at the desk, refusing to speak. Y/N knew he wasn’t going to say anything and looked over at Ben. He looked at her with a mournful yet angry look. Clearly it was something bad.

“Tommy was making fun of me, that Dean’s not my real dad, that I don’t know who my dad is” he told her, side eying Tommy.

Y/N’s heart sank into her stomach. This was worse than she thought.

She nodded, calmly standing up from her desk and walking over to Ben. “Tommy, make your way to the Principal’s office, please. You can explain to him why I sent you, and that Ben and I are on our way.”

Tommy rolled his eyes as he got up from the desk, slinging his backpack over his shoulder as he walked out. She was going to be there soon, so he knew he didn’t have a chance to escape.

Y/N took a chair and placed in front of Ben’s desk, sitting down across from him. After a few seconds of figuring what to say, she clasped her hands as she looked at him.

“I can’t imagine what it’s like to hear what Tommy said to you, Ben, but what I do know is that what you and Dean have is special. He cares a lot about you, and he treats you like you’re his, doesn’t he?” she said, pausing after she asked him a question.

Ben responded with only a nod.

“Then that’s all that matters. You know your relationship with Dean better than anyone, and what others have to say about it, doesn’t change the fact that you’re a family. That Dean’s your family” she explained, with a small smile at the end.

There was a brief pause before Ben finally spoke.

“I’m sorry that I’ve been quiet in class. It’s just weird seeing you around the neighborhood and our street, and then here, too” he said, looking up at her.

She was shocked. That wasn’t what she expected him to say.

She smiled, softly. “It’s okay, Ben. I’m sure it’s strange for me to be friends with Dean and your mom.”

She added Lisa in only for Ben, because she knew they were far from friends.

Ben shook his head. “No, not really.”

Y/N nodded. She was almost hoping he said it was strange, so that not being around Dean would be a bit easier.

“Alright” she said, standing up. “We better get over there.”

“Am I gonna get into trouble for pushing Tommy?” he asked, as he stood up and followed her.

She frowned, not sure what would happen. “Maybe an after-school detention at most, considering neither of you are seriously hurt.”

“Great” he said, rolling his eyes.

Sure enough, as they discussed everything in Chuck’s office, both Tommy and Ben were going to have to do after-school detention, which Y/N was meant to be supervising that day, coincidentally. Tommy apologized to Ben and then both of the boys were off to their next class, albeit slightly late, but Chuck had already informed the next teachers’ of why they would be late. Chuck told her that he’d call the parents as she left his office. She had literally been there a couple of hours ago, for some good feedback and now this happened. Talk about two ends of the spectrum. Though she had to be thankful nothing worse happened to either of the boys.

The length of time seemed to stretch on forever as Y/N waited for after-school detention to be over. There were couple of other kids in there with Ben and Tommy, who looked like he was ready to run as soon as the time was up.

All of them bolted as soon as she opened her mouth to tell them they could go. Ben gave her a small smile as he walked out of the room, which she returned. He was a good kid and didn’t deserve to be talked about the way he was, no kid did. She hoped it wouldn’t weigh heavily on him after this experience. She quickly packed her own things, putting on her dark grey coat over her dark grey A-line dress, with a deep red belt and collar. She was more than ready to go home herself.

* * *

Dean leaned against the Impala, waiting for Ben to come out of the school. He clocked off early to come and get him after he was done with detention, as Lisa was working late. She had called him and told him what happened, and now here was. He smiled as he watched Ben walk out and over to him.

“Hey” he said, putting an arm around him. “You okay?”

“Yeah” Ben nodded.

“Alright, well, you can fill me in on why you had to go to detention on the way home” Dean said, as he opened the car door.

As he was about to get in, he saw Y/N leaving the school, pulling her coat tight around her, protecting herself from the wind. His eyes followed the lines of her legs in her stockings and black heels, shaking his head of the thoughts that flashed through his mind.

“Hey, just wait here, okay?” he said to Ben.

“Sure” Ben replied, not really looking up at where Dean was heading off to, as he got into the passenger side.

Dean jogged up to Y/N, quickly catching up to her. “Y/N!” he called out and watched her turn around.

Y/N was shocked to hear his familiar voice call out to her. She didn’t expect to see him there and swallowed nervously. “Dean, hi.”

“Listen, I know you said that we shouldn’t talk about what happened, but I just… I have to know-” he started but she cut him off, shaking her head.

“You don’t have to say anything, Dean” she said, quietly, her emotions getting the better of her. She didn’t want to do what she was about to, but she had to. “It was a lapse in judgement for both of us. A moment of weakness that won’t ever happen again.”

Dean knew there was truth to her words but hearing them made his heart feel heavy. As much as he was trying in the last couple of days with Lisa, it hadn’t done much for his hopes that they would be fine again. He wanted to talk to Y/N and see if they could work something out.

“I just think-” he started but she cut him off again.

“No, Dean. Just don’t. You have a family. They’re the ones you should be thinking about, not me. That kid over there” she said and pointed to the car where Ben was. “He considers you his family, and I know you feel the same. I won’t break up a family, Dean. I just won’t.”

He looked between the car and her. She was right. He cared about Ben, and he was only in this relationship for him now. To be in his life. Did that mean he had to be miserable with Lisa forever, though? He didn’t know what to do.

“Do you regret it?” he needed to know if she felt the same way as him. He wished he hadn’t done it while he was with Lisa, but it happened. However, remembering how she felt against him… it felt right.

She shook her head, feeling tears prick her eyes. “No. And that’s the problem.”

She should’ve felt regret. She should’ve hated what she did. She felt guilty for it happening but at the same time, she couldn’t regret kissing him. She had never felt a connection like that with anyone she had been with.

“But that doesn’t mean I don’t feel guilty” she said, before pressing her lips together to keep them from quivering. “Ben’s a great kid. At the end of the day… I have to look out for him as much as you do. I’m not his parent but I am his teacher. I have a sense of responsibility to him.”

He felt a pang in his heart as she looked at him, tears threatening to fall.

“I know you have your issues with Lisa, and I want… more than anything, to say forget it all and take me in your arms, but I can’t. I shouldn’t be thinking about you in the ways that I do. I shouldn’t be thinking about what life would be like with you” she shook her head, everything just spilling out in a ramble of emotions.

“Y/N…” he whispered, slowly putting his hand on her shoulder. He wanted to tell her that he thought the same things.

She gasped, feeling the warmth of his hand radiate through her. She gulped and breathed in deep. She looked at him with a stony expression. She had to put her walls up and walk away. It was the only way to save herself from heartbreak and for him to not feel like crap for what happened.

“I’m… going to step back for a while. You’ll see me around, I know, but we have to pretend like nothing happened. You have to think of me as your neighbor, as Ben’s teacher, and that’s it. We can’t be friends anymore, Dean” she said, as a tear finally escaped and rolled down her cheek.

Dean’s eyes widened as he shook his head. “What? No. Screw that-”

She shook her head when he tried take her hand in his. “It’s too hard to be around you and not be with you, Dean.”

“Y/N” he said, finally getting close enough to her that he could take her hand in his and she couldn’t stop him. “Don’t do this.”

“I’m sorry, Dean. I have to. They’re your family and you care about them; I can see that. And I can also see that you care about Ben. So much so, that you’re willing to stay in this relationship for him” she said, smiling sadly. “You’re a good man, Dean. You’re loyal and you’re trustworthy, kind and loving… but at some point, you have to decide whether what you’re staying in this for is a good enough reason.”

Dean stared at her but didn’t say anything.

“It’s a big decision to make… but I can’t make it for you by continuing the way we have been. It isn’t fair to anyone.” Her voice cracked, slightly shaky but she managed to keep the rest of her tears at bay.

Dean shook his head as he looked at her. Everything she said made sense. Despite it, he couldn’t help but feel his heart sink at her words. Not being friends would feel weird, especially if he saw her around and couldn’t say anything to her. Maybe… maybe they needed this, though. He needed to give Lisa a chance without Y/N being a constant in his life. He told himself he would try, and now he had a proper chance to do so.

“It’s gonna be weird… not talking to you” he said, honestly.

She nodded, looking into his eyes. His beautiful eyes that she always lost herself in. “I know.”

“Take care of yourself, Y/N” he muttered, his jaw clenched, eyebrows furrowed.

“You too, Dean” she whispered. “Whatever you decide… just make sure you’re doing the right thing. For everyone.”

She looked at him one last time, and even though she probably shouldn’t have, she leaned in and softly kissed his stubbled cheek. It would probably be a mixed signal, but she couldn’t leave him there looking so sad.

As she walked away, Dean could feel a tingle on his cheek where she had imprinted her kiss, much like she had on his lips, previously. Watching her walk away made his stomach uneasy, feeling it churn as she got into her car. She would be right there across the street, and he wouldn’t be able to talk to her. He didn’t know how to process that as he walked back to the car where Ben was waiting for him.

When Y/N got into her car, she watched as Dean got into the Impala and drove off, the rumbling of the engine reaching her ears, even from this distance.

As she drove home, she knew she had to make peace with her decision. As much as she wanted to take it back, she had to let him go.

Once and for all.

* * *

**2 weeks later…**

Y/N sipped the last of her vodka martini, bopping her head in time to the music. Next to her, Charlie was doing the same. She was glad when Meg suggested they come out to the city for a night on the town, on Saturday night. She needed a night of good drinks, good music, and maybe even a little flirting.

It had been two weeks since she had talked to Dean in the school parking lot. In that time, she had barely seen him. Just once or twice as she left for work in the morning and so did he, and once when she was coming back from the grocery store. She had seen him with Lisa one night, coming back from what looked like date night. She was glad that things were going a bit better for them, but it didn’t mean it didn’t hurt seeing them together.

Which is why when Meg had suggested they drive up to Kansas City to go to a bar she liked; Y/N jumped at the chance. As Lizzo serenaded her from her “Badass Women” playlist, she put on a black lace bodysuit and mini leather skirt that came to her mid-thigh, her black lace up heeled ankle boots, gave herself a smokey eye with lots of mascara look and a plum colored lip. She put a bit of wave in her Y/H/C hair, smiling at the way she looked. Charlie had whistled when she opened the door as shrugged on her long black coat, and she had laughed a little nervously when Meg told her she was “totally gonna get laid tonight.” It was her first time meeting the dark-haired woman in person, and she liked her instantly. She had like her even as they chatted over the phone, but it was different now. She seemed like a take-no-shit type of person, and Y/N liked that.

While she wasn’t expecting anything tonight, Y/N felt confident in the way she looked, having caught a few eyes on her already. Being here had given her a confidence she had been lacking back home, because of all the emotional and mental abuse Ethan had put her through. When Dean told her he admired her strength, that she was beautiful and an incredible person, it awoke something in her. She felt different. She didn’t need validation from anyone, but at the same time knowing that she was appreciated and loved by these amazing people she had met, gave her a new sense of belonging. She finally felt like she was exactly where she needed to be.

Meg pushed her way through the crowd of people, a tray of drinks in her hand. She handed her and Charlie their respective drinks, taking the Shirley Temple for herself, as she had made herself the designated driver.

“Y/N, there’s a group of guys over there, and I swore the blonde one is totally looking at you” she said, pointing discreetly over her left shoulder.

Y/N frowned and looked around, sure enough seeing 4 guys around a table like the girls were, the blonde one looking in their direction.

“He could be looking at you, you know. Or Charlie. I mean he doesn’t know you’re both taken” Y/N shot down the idea.

Charlie scoffed. “Yeah, right. All eyes have been on you tonight.”

“Go over there” Meg told her, her eyes lighting up.

“No” Y/N said, shaking her head.

“Do it or I will” Meg threatened, smiling wickedly.

“You wouldn’t, Masters” Y/N glared at her.

“Watch me, Y/L/N” she laughed as she quickly dashed off.

“Meg!” Y/N called out but she wouldn’t be heard over the music.

Charlie laughed as she took a sip of her drink.

Y/N shook her head at her and took a sip of her martini.

Y/N watched as Meg talked to the blonde guy and then pointed over at her. Y/N gulped nervously when she saw him nod. He was looking at her. Shit. Meg quickly walked back over.

“Girl, he’s so interested! Come on, please go over there” Meg was practically shaking with excitement.

Y/N sighed nervously. Was she ready for this?

It had been a year since she and Ethan had broken up. In that time, she had hooked up twice on two different occasions, back home. It had felt good to just have sex for the release she had needed, but it had been a while since she let herself feel something more for a man. Dean was the first one she had felt a strong connection to since Ethan, back when things were still okay with him. Even then, the pull she felt towards Dean was unlike anything she had ever felt. Not with Ethan, or any other boyfriends from the past.

What she felt for Dean… it still hadn’t fizzled out, as much as she tried to ignore it. Maybe this is what she needed though. To get over him.

She rolled her shoulders back and fixed her hair. “How do I look?”

“Sinful” Meg replied, simply.

She laughed, shaking her head at her new friend. “Okay. I’m going.”

Charlie grinned. “Go get him.”

Y/N hopped off the high-top stool and moved through the crowd. As she did, her Y/E/C eyes connected with his, and he flashed her a smile. She smiled back as she reached the table, his friends quickly excusing themselves. As she got closer and could see him properly in the dim lighting of the room, she saw that he had blue eyes. He was only a few inches taller than her because of her heels, unlike Dean who would tower over her no matter her footwear.

“Hey, I’m Mark” he said, offering his hand.

“Y/N” she took his hand and shook it. She didn’t feel a spark just yet from his touch like she had with Dean so instantly, but that was okay.

“I’ll be honest, I couldn’t stop looking at you all night” he laughed, sounding a little nervous.

She felt the heat rise in her cheeks, and it wasn’t from the alcohol. “Well, you’re not so bad yourself.”

“Let me get you a drink” he said, flagging down a waiter. “What’ll you have?”

“Vodka martini” she said, and watched the waiter walk away to get her a drink. She could’ve just gotten hers from her table, but he had offered to buy her one. She couldn’t say no.

“Thanks” she said, smiling at him.

“You’re welcome” he smirked.

“Do you live here in the city?” she asked, as the song overhead changed to something slower, making it easier to talk.

“Yeah. You?” he asked in return.

“Lawrence” she replied.

“So, what do you do, in Lawrence?” he wondered, smiling at her.

“I’m a teacher, 8th grade English” she smiled back.

“Wow, that’s great” he nodded, approvingly.

“What do you do?” she asked.

“I’m a copywriter, for an ad agency” he replied, handing her the glass as the waiter came back to them. He passed the waiter a few bills before he walked away.

She nodded, approvingly, too. “That’s amazing.”

“Not as glamorous as you would think, though” he laughed, slightly.

“Ah, so nothing like a modern version of Mad Men?” she joked.

He laughed loudly, shaking his head. “Definitely not.”

With a break in conversation, Y/N drifted off as the song that started while they were talking, continued. The words hit her as she thought about her life back home, and the life she was making for herself now, starting over in Lawrence. The song spoke of a person to start over with, and while she longed for that someone to be Dean, she knew it couldn’t be.

_It don’t matter to me_

_Wherever we are is where I wanna be_

_And, honey, for once in our life_

_Let’s take our chances and roll the dice_

_I can be your lucky penny_

_You can be my four-leaf clover_

_Starting over_

“Hey” Mark’s voice bringing her back to reality. “You alright?”

She smiled, nodding quickly. “Yeah, I’m fine.”

“Just feeling the song, huh?” he asked, laughing.

“I guess” she shrugged.

They talked for a few more minutes before his friends came over and told him they were going to head out.

“I should probably go, too” he said, regretfully. He took out his phone and handed it to her. “Here, put your number in and we can talk some time. Maybe… maybe I can take you out some time?”

She smiled as she typed her number in. A flashback of doing the same thing with Dean’s phone passed through her mind, but she pushed it away. “Yeah.”

“It was nice to meet you, Y/N” he said, smiling.

“You too, Mark” she smiled back, biting her lip.

As he left, she sighed. He was nothing at all like Dean, as she had discovered through their initial conversation. They were completely different in their features, the way they dressed, and the way they talked. Maybe that was a good thing, though. Giving Mark a shot would be the best way to detach herself from Dean. He was adorably cute, and she liked their banter already.

Maybe Mark was what she needed to truly forget about her feelings for Dean.

* * *

Dean popped the last bite of his burger into his mouth, humming as the flavors exploded on his tastebuds. He leaned back and took a sip of his beer from the bottle, glancing around the diner. It was a favorite spot for him, Ben and Lisa and they used to come here quite often before things started going sour. Funnily enough, it was Lisa who had suggested they go out for dinner and go there.

Things had been slightly better with her these last couple of weeks. They had managed to have proper conversations without things getting out of hand, and he had even made her laugh a few times. There was still no dice in terms of sex, but he was hoping that would change tonight when they got back home.

Dean looked over at Lisa and Ben sitting across from him, currently having a slight disagreement over him playing games on his phone while they were out and eating dinner.

“Hey” Dean said, interrupting them. “Listen to your mom.”

“Fine” Ben said, rolling his eyes as he put his phone away. “Can I at least get a refill?” He shook his empty glass.

“Yes” Lisa said, smiling slightly.

Ben got up from the table and went and stood in line at the self-serve refill station.

“Thanks” Lisa said as she turned to look at Dean.

“No problem” he said, winking at her.

He smirked when he got a small smile out of her. He couldn’t believe how things were suddenly looking up for them, but he was relieved to not be fighting with her for a change.

Her phone chiming once, then twice got his attention as well as hers. She looked at her phone, but quickly pushed it aside.

“Something wrong?” he asked, frowning.

“No, just my sister. I’ll talk to her later” she replied, shaking her head.

“Lis, it’s your sister. Talk to her, I don’t care” he shrugged, not minding if she took a call.

“No, it’s really okay” she said, her voice shaking a little.

“Lisa, what’s going on?” he asked, starting to suspicious that something was up.

“Nothing” she bit out through gritted teeth.

Dean sighed, annoyed when the phone chimed again. Having spoken to her sister a few times, he figured he’d talk to her and see if everything was okay. He reached across the table and picked up Lisa’s phone.

“Dean!” she protested.

“If you won’t talk to her then let me” he said, looking down at the screen. He glared at the screen as he read the messages. They weren’t from her sister.

_Call me when you’re done with dinner._

_I can’t stop thinking about you._

_I wish you were here with me._

Dean saw that there was no name, just a heart emoji instead. He read the ones on the lock screen, and that was enough for him to get the picture. That was enough for him to know that she was still lying to him. That she had been for more than a year now.

Dean looked at her and saw her face change into fear.

“Something you wanna tell me?” he asked, glaring at her.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	7. A Lesson in Denying Feelings

**Summary for the Chapter:**

> Dean learns the truth about what Lisa’s hiding, and makes a decision. Later, Y/N goes on a date with Mark, knowing she needs to move on. However, after a failed attempt to move things to the next level with Mark, she begins to question whether she should be denying her feelings for Dean.

**Notes for the Chapter:**

> Warnings: Swearing, Angst, Insecurities, Denying Feelings, Jealous Dean, Pre-smut (nothing too graphic yet, pretty much ends before it starts)

* * *

Dean stared at Lisa, his eyes glaring as his jaw clenched. He was waiting for her to say something about what he could clearly see on her phone. He had really hoped that making the effort was going to pay off, and that they could finally be happy again. He thought about how he had doubted her in the past, over a year ago, when she had gone back to Indiana for a couple of weeks. She came back completely disinterested in him and their relationship.

They had fought a lot about whether she had slept with someone else. She had denied it and he had chosen to believe her, even if he did have his doubts about it. Since then, is when things turned for the worst. He thought he had judged her too quickly. Maybe nothing had actually happened.

Turns out, he had been right all along.

Lisa shook her head, not being able to say anything. Dean could tell from her expression that she was trying to find a way to say something.

“I don’t know what to say-” she started but he cut her off.

“Don’t” he hissed, as he leaned in so no one would hear their conversation. “I’m only gonna ask this one more time, and you better give me a straight answer.”

When she didn’t say anything, he continued.

“Did you sleep with someone else?” he asked, bluntly. He had asked that very question a year before, when she got back from Indiana. He never got a proper answer from her.

Lisa was quiet as she sat across from him. She looked up at him, and he saw sadness in her eyes for the first time in a long time.

“Yes” she whispered.

He nodded as he stared at her. He huffed a laugh and it bubbled into a bitter tone. “Who’s the guy?”

She took another few moments to say anything. “His name’s Matt. He’s a doctor.”

“Oh, Doctor Matt. How respectable” he snapped.

She looked guilty as she dropped her head, avoiding his gaze. “I’m sorry you found out like this” she said, quietly, but Dean heard her.

“Why did you keep this going for another year? Why didn’t you just answer me when I asked? This could’ve all been over then, and we could’ve forgotten about each other” Dean asked, shaking his head.

“Because… Ben really looks up to you, and I wanted a father figure for him” she replied, as she looked up at him, her eyes glistening.

Dean shook his head, confused. “But what? Suddenly I’m not good enough? You want some doctor for him to look up to instead now?”

“Matt and I fell for each other years ago, but it didn’t go far, and then I was there last year… we started things up again, and when he was here in July-” she rambled, trying to explain but Dean cut her off when something occurred to him.

“He was here?” he asked, as he stared at her.

She only nodded.

“That’s why we stopped having sex.” He didn’t need to ask because it was obvious why.

An uncomfortable silence fell between them.

“So… when should we tell Ben?” she asked, quietly.

“I’m gonna leave that to you” he replied, shaking his head. “But when you decide to leave… you’re gonna let me say goodbye to him. You owe me that much.”

He looked at her as he waited for a reply. She nodded as she continued to stare at him.

“Dean-” she started but he cut her off.

“Save it” he growled; his jaw clenched. “It’s done.”

She nodded and didn’t say anything else, as Ben returned to the table unaware of what had just occurred.

As they went about like nothing had just happened, Dean couldn’t help but think that maybe he didn’t deserve to be angry. After all, he had kissed Y/N and it had made him feel awful for doing that to Lisa, despite the fact that he couldn’t stop thinking about his beautiful neighbor. So, did he have the right to be angry with Lisa when he had done that? He came to the conclusion pretty quickly. Yes, he did have the right. Lisa had lied to him for a year, she had slept around with that guy behind his back and didn’t seem to regret it at all. Her sadness came more from the fact that Dean had found out. It wasn’t “I’m sorry I did this to you” it was “I’m sorry you found out like this”.

So, yes. He did deserve to be angry and to be the one to end the relationship.

When they got back home, Lisa went into Ben’s room to break the news. Dean wasn’t sure what she told him, about whether or not she said she had met someone else or not. Quite frankly, he didn’t care. He kicked back on the couch with a beer, some re-runs of M.A.S.H. on the TV keeping him entertained. He heard some yelling from Ben and then a door slam, and then another one close a bit more gently. Dean would eventually go in and see how Ben was taking the news but for now… he was taking a moment for himself.

For the first time in a long, long time, he felt lighter. He felt better, and in a weird way, as much as it hurt to hear that Lisa had cheated on him, he was relieved. He finally got the answer to his question, and now… he could finally move on. He could concentrate on his business, be available to his family more, and just be himself without worrying what Lisa would say. All the constant fighting or ignoring each other and pretending to be civil was over. He had been down the road with her several times in the last couple of years, the road of things being fine and then not fine, but he was never going back to that again.

He was looking forward to living his life the way he wanted again.

* * *

Over the next week, Y/N and Mark texted back and forth. There were messages about their days, what they had for lunch or dinner, silly jokes and flirty comments. Y/N liked him enough, but she hoped that he did ask her out so that she could get to know him more.

**Mark:** _I can’t beat around the bush anymore. I really want to take you out. Saturday night, 7pm?_

Y/N had agreed instantly and tried to protest when he said he would drive to Lawrence and have their date there, but he insisted. She wanted to avoid anyone seeing them, or even possibly running into Dean, but she supposed she couldn’t ignore that fact. She just hoped she could avoid him, though.

The restaurant buzzed with sounds of chatter from patrons and the soft jazz music playing through the speakers. Mark sat across from her, dressed in black jeans and deep green v-neck sweater, while she had adorned a silk navy blue strappy top, with black jeans and her long fawn coat, that was hanging off the back of her chair.

“This place is great” he said, as he looked around the room.

“Yeah, the food’s really good and the drinks are even better” she said, as took a forkful of her meal. It was the same place she had come to with Charlie for drinks. She loved the vibe there.

“So… what’s 8th grade teaching like?” he asked her.

She laughed a little, putting her fork down. “Challenging. It’s an interesting age for kids, they don’t really want to be told what to do but they know they have to. It’s rewarding though, especially when their faces light up because they’ve done well on a test or homework.”

“I suppose it helps they have a teacher as passionate as you” he complemented her.

It was nice of him to say that but somehow when Dean had some similar words to her, it was easier to believe him.

“Thanks” she said, accepting the complement with a smile. She needed to give him a chance.

“I gotta ask though. You said you’re from upstate New York. Why such a big move to Lawrence, Kansas? Of all places” he inquired with a laugh.

She smiled slightly, her muscles not committing to a genuine one. It was touchy subject, something that she couldn’t tell him just yet. She had told Dean, which she never expected to do so soon into their friendship, but she had trusted him. He made her feel safe to tell him, even in such a short time. It wasn’t going to be the same with Mark.

“I just needed a change, a new experience” she replied, not even remotely divulging the real reason.

“Fair enough” he nodded, taking a sip of his wine.

“What about you?” she asked, changing the subject. “What’s a day in advertising like?”

“Stressful” he huffed. “Not nearly as rewarding as teaching, but there are days when things go well, and you can relax for a small fraction of time. Then it’s just back to the grind, not a whole lot of time to appreciate your achievements.”

“But you love it, right?” she said, shrugging.

“Yeah” he said, simply as he went back to eating.

The rest of their conversation was light-hearted and fun, and Y/N was surprised at how much of a great time she was having with Mark. She thought that wouldn’t happen so soon, but she was glad that it had.

* * *

Dean got out of the shower, quickly drying off before getting dressed into jeans and a thicker white Henley, now that the weather was starting to turn. He was going to the bar tonight, with Cas and Benny joining him. It been a week since he and Lisa broke up. The day after it happened, Lisa took Ben and herself and some of their necessities to a hotel. During the week, she had been over a few times to pack up her things. It seemed like it would take a little while longer for her to completely clear her things out, but at least she was doing it while Dean was at work and he wouldn’t have to see her.

Dean drove to the bar, his thumbs drumming against the steering wheel as he listened to his music, loudly. When he arrived at the bar, he ordered a neat double of his favorite whiskey. As he sipped his drink, he frowned as he heard the words to the song that were playing.

_You want commitment, and take a look into these eyes._

_They burn with fire, yeah, until the end of time._

_And I would do anything, I’d beg, I’d steal_

_I’d die to have you in these arms tonight._

He shook his head as the words hit home to what he was feeling. He may have rocked on occasion, but Dean hated Bon Jovi with a passion in that moment. He was trying not to think about Y/N. Nights out with Lisa had helped, but then something or other would remind him of her and he’d start thinking about her again. Now that things were over with Lisa, however, Y/N had been a constant thought in his mind this past week.

As he was hunched over on the table, he felt a pat on his back. He looked up to see Benny sit down in front of him, Cas not too far behind as he took the chair next to Benny.

“Good to see ya, brother” Benny commented, a big grin on his face.

“You get laid before getting here?” Dean asked, taking in his friend’s expression.

Benny chuckled, as the bartender came over and put a glass of whiskey down in front of him and Cas. “I don’t kiss and tell, Dean.”

Dean shook his head, rolling his eyes with a small smirk. He lifted up his glass as they all clinked theirs together.

“You seem… not grumpy” Cas commented, as he took in the lack of a scowl on Dean’s face.

Dean shrugged. “Things are… I don’t know, better”

“Really?” Cas asked, confused.

“Yeah” Dean nodded, simply. He hadn’t told his friends yet as he wanted to wait to get them to a bar to break the news. “I broke up with Lisa.”

Both Cas and Benny were in shock, their eyes widened. Cas sat forward as he squinted. “Seriously?”

Dean nodded, sipping his whiskey.

“Well… I never thought I’d see the day that happened” Benny said, shaking his head, with a smile on her face.

“Hilarious” Dean said, rolling his eyes.

“And you’re really… okay?” Cas asked, concerned.

“Yeah, man. I really am. I probably should feel worse, and I do, considering Ben was pretty upset. When it comes to Lisa, though… yeah. I’m good” Dean replied, truthfully.

“What happened?” Benny asked, curiously.

“Turns out, I was right. She cheated on me with some guy she used to know, when she went back to Indiana last year” Dean replied, staring down at the table.

“Damn” Benny whispered, shaking his head.

“Yeah” Dean agreed, sipping his drink. “Her phone was in front of me and I saw his messages. So… I ended it.”

“Good for you, brother” Benny said, clinking his glass with Dean’s.

Cas did the same with his glass against Dean’s.

“So, what now?” Cas asked, taking a sip of his drink.

“I don’t know” Dean shrugged, as one side of his mouth lifted up into a half smirk. “Something different, I guess.”

“What was that?” Benny asked, eying him suspiciously.

“Nothing” Dean replied, his eyebrows furrowed.

Cas leaned back in his chair, silently questioning Dean. “Does this have something to do with Y/N?” Cas asked, something occurring to him suddenly.

“No” Dean said, too quickly.

“Oh, it so does” Benny laughed slightly.

Dean looked between his friends, not knowing whether he should say anything or not. He hung his head, giving up the pretence.

“Yeah, it does” he said, his voice low but they heard him anyway.

“I should’ve known something was up when you were both making eyes at each other at the garage” Benny said, smiling wide.

“Nothing’s up, okay? Nothing happened” Dean lied yet again.

“That didn’t sound true, did it?” Cas asked Benny, knowing their friend well.

“Nope” Benny replied, popping the ‘p’.

They looked at him and he couldn’t deal with their knowing stares.

“Fine” Dean sighed, exasperated. “We kissed.”

“Dean” Cas groaned.

Benny let out a long whistle. “Damn, brother.”

“Yeah, I know, I know what you’re gonna say. It was a mistake, I shouldn’t have done it, I know I shouldn’t have. Okay?” Dean grumbled. “It’s just… I can’t stop thinking about her.”

“Do you like her?” Cas asked, genuinely wanting to know. He knew what his friend was like before he met Lisa, and he wanted to make sure he wasn’t reverting back to his old ways.

“Fuck, this is like high school” Dean mumbled, sipping his drink. “Yeah, I do. I like her. I mean, it’s more than that… I’m really falling for her.”

“And you haven’t told Lisa?” Cas asked, sitting forward in his chair.

Dean rolled his eyes and glared at him. “Well, I don’t think I have to now considering we’re not together and she actually cheated on me. This was just a moment of weakness.”

Cas nodded. “I guess you’re right.”

“Hey.” Dean leaned forward in his chair as he looked at both of them. “It was a mistake, the way it happened. I know that. Y/N said that she wouldn’t let it go any further as long as Lisa and I were together, and I agreed with her.”

“No wonder you two haven’t spoken in weeks” Cas muttered.

“Yeah” Dean scoffed, nodding. “It’s just… now that Lisa and I are over, I don’t know, but – maybe now I got a shot with Y/N.”

“Maybe” Benny said, a small smile on his face.

Dean looked at Cas and thought about whether or not he should ask about Y/N, but he needed to know.

“How… how is she?” he tried to ask as casually as possible.

“She looked pretty sad for a while. I guess we know a little about why now. She’s been better in the last week, though. She’s uh…” Cas replied, but he didn’t know how to broach the next subject.

“She’s what?” Dean was concerned as he asked the question.

“Y/N’s on a date. Some guy she met in the city when she went out with Meg and Charlie last weekend. It’s their first date tonight” Cas told him.

Dean’s jaw clenched as he looked down at the table. “Who’s the guy?” He looked up at Cas, his expression hard and distant.

“Mark something, I don’t know who he is. She seemed excited about tonight though” Cas replied, trying to gage some kind of reaction from Dean.

Dean huffed as he looked down at the table. She was on a date with some guy. Mark. She was moving on from him, and while Dean wanted to find the guy and tell him that he couldn’t have her, he knew she was right in moving on. She wasn’t anything to him for him to get protective of her. Maybe Mark was a nice guy and after what she had been through, she deserved a nice guy.

“Well…” he sighed, throwing his head back as he finished his drink. “Good for her.”

Benny knew that look on his friend’s face. “You alright there, brother?”

“Oh yeah” Dean replied, twirling his glass around in his hand.

“Dean-” Cas started but Dean cut him off with a glare.

“I’m gonna head back” he muttered, standing up from the table. He dropped a few bills on the table, before picking up his jacket.

“Thanks for tonight, fellas.” Dean walked away, without looking at his friends.

When he got back home, he poured himself another whiskey and sat down on the couch. He leaned his head back and closed his eyes. He kept thinking about how life would’ve been if Y/N hadn’t moved across the street. He may never have realized that he and Lisa were in a meaningless relationship, and probably would’ve kept going the way they had been for many more years.

Y/N encouraged him to go ahead with his plans for expanding the garage, a move he was scared to make, but he couldn’t wait to get started on that. She talked to him about all his likes and dislikes, listened when he talked about his family, and told him that maybe he and his dad still have to work out some things from the past. She trusted him enough to tell him about her previous relationship and what her asshole of an ex did to her. She cared about him and he cared about her. Hell, he was really starting to fall for her, but he had to respect what she wanted. Yes, it was a first date with this guy, and she might not want things to go further, but she deserved to give things a chance without him being a factor. She deserved to be happy.

Dean frowned and lifted his head, as he heard a car from outside, the breaks squeaking softly as it pulled up to the curb. He stood up and slowly walked to the window, his heart sinking when he saw Y/N get out of the car. She was coming back to her house with her date.

Mark drove her home, chatting and changing songs in the car to suit their mutual tastes, which she quickly learnt were quite similar. He wasn’t much for classic rock, but more for the folksy stuff of now. They kept the small talk going as he pulled up outside her house. She quickly got out of the car and walked to her front door as he walked beside her. She turned to him and smiled as they stood outside her door.

“I had a really great time” she smiled. There was definitely promise of more and of better, and she was going to give him the chance.

“Me too” he smiled in return.

He slowly and tentatively leaned in, kissing her cheek, softly. She smiled wider at the sweet gesture.

“Goodnight, Y/N” he whispered as he moved back.

“Goodnight” she said, watching him leave.

As she watched him drive off, she sighed. There was something there, and while she didn’t know what it was, she knew she had to take a leap and find out.

She really needed to call her sister and talk about this with her soon.

Dean watched as the guy leaned in and kissed Y/N’s cheek, very relieved that he hadn’t kissed her on the lips. She looked happy, and that’s what mattered. It was what he wanted for her. Even if he wasn’t the one to do that for her.

* * *

**2 weeks later…**

Dean had come to a conclusion about Mark. He hated the guy.

It had been two weeks since Y/N and Mark’s first date, and in that time, he had seen them together around town quite a few times. They would be talking and laughing, kissing and being happy and honestly, it made him sick. To someone else, it may have looked like he was jealous, and maybe he was a little, but he was mostly concerned for her and hoped that she had made the right decision. It was irrational to hate him based on all of this, considering he had never met the guy, but he couldn’t help how he felt.

The alarm blared obnoxiously, even though Dean had been awake for a few minutes already. He tapped it hard and turned it off, his hand combing through his hair. He got up and dragged himself into bathroom, quickly brushing his teeth and freshening up. He had opted to have a shower when he came back from doing some manual labor.

He got dressed in his worn jeans, dark brown Henley and a brown and white plaid shirt over the top, his black jacket over that and walked through the house. He picked up his wallet and keys and then left, firing up his Baby and driving away from the house, as his music blared. He made a quick stop to pick up three coffees from the coffee shop, and then drove for about 15 minutes, before reaching another street. He drove down, past all the pristine houses, until he came to the one he was looking for.

He looked up at the house as he got out of the car. It had seen better days and he had bought it for a steal a few months ago. With the help of Cas and Benny, he was going to fix it up and make it a home. They would do what they could until builders came in at a later stage and did all the more complicated things like wiring and plumbing.

As he walked into the house, his mind started thinking in overdrive. Throughout his time as a bachelor, he was the love ‘em and leave ‘em type of guy, opting for one-night stands rather than proper relationships. It was fun and easy, but over time he had gotten over that. Cassie was his first serious girlfriend when he was 24, and they dated for 6 weeks. He had cared about her, but they weren’t meant to be. He dated girls and continued his one-night flings for a few years, before he met Lisa. She didn’t end up being just a one-night thing, and he really thought that they would be great for each other.

While being every woman’s “Mr. Right Now”, Dean had always longed for something more, even if he didn’t admit it to anyone. He barely admitted it to himself. That being said, he used to have a recurring dream. A beautiful woman in a beautiful house, welcoming him with a passionate kiss as he came home from work. They had three children, 2 boys and a girl. He couldn’t see their faces, as it was a fantasy in his mind that would never come true. When he met Lisa, the woman had morphed into her. However, as they started to have their problems, the woman became faceless again.

Standing there in the house at that moment, images of the dream started to flash before him. The woman had a face again. This time… it was Y/N. He suddenly began to imagine her in this house with him and Dean’s heart began to beat rapidly at the thought. She belonged here. He wanted her here with him. He wanted a life with her. He couldn’t want that. He tried hard to turn the image of Y/N back into a faceless woman, but nothing happened.

He was 34 years old and his little brother had gotten married before him, and would no doubt tell him that they were having kids soon. He loved his brother and sister-in-law, but every time he looked at them it was a reminder of the fact that he may never have that. He never thought he wanted those things, but this recurring dream always told him otherwise.

A slap on his back startled him out of his daydream. Benny walked around him with Cas right behind him.

“You okay, chief?” he asked, picking up the coffee with his name on it.

Dean nodded, blinking a few times. “Yeah. Fine.”

“You sure?” Cas said, concerned when seeing his friend looking slightly out of it.

“Uh… yeah. I, um… just have a few things on my mind” Dean said, looking around the house.

“Well” Benny started, lifting up a sledgehammer. “Nothing like breaking some shit to clear your mind.”

Dean huffed a laugh and took the tool from him, walking over to the nearest wall and getting to work.

* * *

Y/N pushed her sunglasses up and pulled her brown checkered coat a little tighter around herself. Despite the sun, there was a chill in the air as brown leaves brushed over the pavement. She sat outside a café, waiting on Charlie and Meg to get there for brunch. It was Sunday and Meg always had them off, so they were taking the opportunity to see each other. Her foot tapped along to the song that came from the café, the leaves making a crunching noise as they caught under her shoe. She smiled when she saw them walking up the sidewalk, both bundled up as well. The fall was in full force and it wasn’t Y/N’s favorite in terms of weather, but she had to admit, it was incredibly beautiful as she admired the leaves changing color.

She sat up a little and kissed them both on their cheeks, as they sat down across from her. She smiled as she watched them settle in.

“I’m starving!” Meg groaned, as she looked at the menu.

“Hello to you, too” Y/N laughed at her dramatics.

“We better order quick before the demon comes out” Charlie joked, earning a side eyed glare from Meg.

Y/N laughed as she called the waitress over and they all ordered, after Charlie and Meg quickly decided what they wanted.

“So, how are things going with Mark?” Meg asked, getting straight to the point.

Y/N shrugged, knowing there wasn’t much to tell. “It’s been a good two weeks. I’m having fun with him. He’s a great guy. We’re seeing each other again tonight, for a movie.”

“That’s so great, Y/N” Charlie beamed. “I’m so glad you’re happy.”

Y/N smiled, nodding. “I am.”

Mark made her laugh and forget about everything that had happened before they met, but at the same time, she was still waiting to feel the sexual chemistry with him.

“He’s coming to your birthday dinner on Friday, right? We gotta meet this guy properly” Meg asked, as the waitress came back with their coffee orders.

“Yeah, he is. So, you can assess him then” Y/N laughed, as she took a sip of her coffee.

Charlie joined in but stopped as she wondered if she should ask Y/N what she wanted to ask at that point. “Have you… have you talked to Dean at all?”

Y/N sighed as she looked at her friend, and then shook her head after a few seconds. “No.”

“You really want to cut off from him completely?” the redhaired woman asked, her face morphing into sadness.

“I think I have to” Y/N replied, as she avoided her friend’s gaze. She knew that if she looked at her, she’d change her mind, and she couldn’t do that.

Charlie bit her lip as she and Meg looked at each other. Meg nodded, and Charlie turned to Y/N.

“What?” Y/N asked, knowing something was up.

“Y/N… Dean and Lisa broke up” Charlie told her.

Y/N felt her breath catch in her throat as her eyes widened. That was the last thing she was expecting Charlie to say. “W-When?”

“A few weeks ago” Meg replied, her fingers tapping against her coffee cup, nervously.

Y/N scoffed, shaking her head. “And you’re telling me this now?” She was annoyed that they hadn’t bothered to tell her this for weeks.

“We wanted to, we really did” Charlie reasoned. “But Y/N, things seemed to be going great with Mark, so we thought we shouldn’t.”

Y/N looked between them. She sighed, looking down at the table and fiddling with the cutlery. “I guess you’re right.”

“It’s just that after that night,” Meg started, putting her coffee down after taking a sip. “You seemed pretty ready to move on and let him deal with whatever happened with Lisa.”

A night out with just Meg a little over a week ago, Y/N had told her what had happened with Dean. She was sure that Cas knew from Dean considering they were best friends, but she was glad that he kept it in confidence that he knew and didn’t tell Meg, despite them being a couple.

“Yeah” Y/N nodded, but her mind was a whirlwind of thoughts at that point. “What happened?”

“He found out about her cheating on him” Charlie replied, sadly.

Y/N’s eyes closed as she shook her head. She couldn’t believe it. Her heart was breaking for him, and all she wanted to do was go over to him and see how he was doing.

“Y/N” Charlie said, trying to get her attention.

YN shook her head as she looked at her friend, having spaced out for a few moments.

“You okay?” Charlie asked, knowing that she wasn’t but asking anyway.

“Yeah” Y/N nodded, smiling. It didn’t really convince her friends. “I’m good.”

Y/N was thankful as their food arrived and it distracted them from what they were talking about.

As Meg told them about something that had happened at the hospital recently, Y/N spaced out again. She couldn’t believe that Dean actually broke up with Lisa. Knowing the reason though, she was glad that he finally had, even if finding out she was cheating on him was the most awful thing that could ever happen. Now, Y/N found herself at a dilemma. Dean was suddenly single, and she was with someone. She really liked Mark and she was having a great time with him. She wasn’t about to break up with him just to be with someone else, but her mind kept floating back to her green-eyed neighbor. She told herself it wasn’t a good idea for several reasons.

One, she was with Mark and she was having a wonderful time with him. Two, Dean had just gotten out of the relationship and he needed some time to himself. Three… she was Mark. She couldn’t break his heart just to be with someone else. She really liked him, and he even kept her mind off Dean, sometimes. So, she wasn’t going to do anything about this new information of the breakup.

It was officially time to move on.

* * *

Y/N smiled as she walked hand-in-hand with Mark, down the sidewalk. They had just watched a movie and were walking back to the car, Mark insisting on driving her to and from their movie date. The night air was chilly, and they were thankful they were both rugged up; Mark in a long black coat over a white sweater and jeans, Y/N in a thick, high neck grey sweater, jeans and ankle boots. They were walking in content silence, but every now and then Mark would lean in and kiss her head. It had been two weeks for them and while Y/N was happy with where things were with them, she had a feeling that things were going to progress every soon. They had had several make-out sessions on her couch, but they were still yet to do anything else. It might’ve felt like it was too soon, but she really did like him and she felt they were ready to take the next step in their relationship.

As they were walking down the sidewalk, they walked past a few bars and restaurants. Suddenly, Mark’s path was cut off slightly as someone walked out from a bar and onto the sidewalk.

“Oh, sorry, man” Mark said, looking at him.

The guy turned to face them, and Y/N felt her breath stop as she saw Dean. He looked so good, wearing a leather jacket over a red and black plaid and dark blue jeans. Dean looked between her, the guy she was with and their hands joined together. _So, this is him_ he thought as he looked at Mark.

“It’s okay” Dean said back. “Hey, Y/N” Dean said, looking at her.

“Hi, Dean” she tentatively smiled.

“You both know each other?” Mark asked, confused.

“Uh, yeah. Dean’s my neighbor” Y/N said, looking up at Mark. “Dean, this is Mark.”

Y/N watched as an older man walked out of the bar and up to Dean, looking at him.

“Everything okay?” he asked him, as looked at her and Mark.

“Yeah” Dean nodded quickly. “Dad… this is Y/N my neighbor and this is Mike” he said, introducing them.

“It’s Mark” the man in question corrected Dean.

“My mistake” Dean said, trying to give him a polite smile, but it didn’t move far enough on his face to be genuine.

Y/N took a deep breath. This was the moment she had feared most. She decided to ignore it, as she smiled at Dean’s father.

“It’s so wonderful to finally meet you, sir” she said, offering her hand. “Dean’s told me a lot about you.” She felt Mark looking at her and knew she was going to get a lot of questions later.

“Well, Dean hasn’t told me anything about you, but it’s still great to meet you, as well” John said, shaking her hand as he glanced at his son.

“We should really go” Dean said, looking between the couple and his dad.

“We should too” Y/N said, looking at Mark.

“Great to meet you, man” Mark said, offering his hand to Dean.

Dean looked down at it for a second, before he shook it. “Yeah.”

As they all dispersed, and Y/N walked back to the car with Mark, she was practically hyperventilating at the thought that Mark and Dean had now met. Albeit briefly, but they had. Dean who she had kissed. Dean who she was trying to deny her feelings for but failing miserably.

She was suddenly wishing for the floor to open up and swallow her whole.

When they got back to her house and Mark took off his coat while she kicked off her shoes, the content silence they had before meeting Dean, was now awkward. Y/N filled two glasses of water and handed one to Mark, as she waited patiently for him to say what she knew he was thinking.

“So… did something between you and Dean?” he asked, looking up at her from his glass.

She shook her head. “No.”

“Really?” he asked, raising an eyebrow. “Because it felt a little-”

She walked over to him, cupping his jaw in her hands. “Mark, nothing ever happened between Dean and I. He was a good neighbor, invited me for dinner one night and told me a little about his family. That’s it.”

She came to the conclusion that he didn’t need to know what really happened. It was before she met him, and it shouldn’t affect them considering she didn’t know him then.

Mark sighed as he looked at her, a small smile appearing on his face. “Okay.”

She smiled and leaned up, kissing him softly. It didn’t take long for Mark to deepen it, as they wrapped their arms around each other.

“Hold on” he said, pulling away from the kiss and taking out his phone, connecting it through Bluetooth to her speaker.

_So long, I’ve been looking too hard, I’ve been waiting too long_

_Sometimes I don’t know what I will find, I only know it’s a matter of time_

Y/N laughed a little at the cheesy song choice but smiled up at him as he pulled her closer and wrapped his arms around her waist, swaying side to side. She wrapped her arms around his neck as he leaned down, kissing her, passionately. Things began to heat up, as Y/N cupped his face, kissing him firmly. She nipped at his bottom lip and opened her mouth, their tongues meeting. He was a good kisser, even if he wasn’t quite the kisser a certain someone else was. In that moment, however, she didn’t want to think about her gorgeous green-eyed neighbor.

Mark walked them back to the couch, helping her lie down. Y/N looked up at him as she undid her jeans and pushed them down her legs, throwing them on the floor. He looked down at her, his eyes dark with lust as he lowered himself and wrapped his arms under her, pulling her close. His hands pulled her high collar down as his lips moved down her jaw, nipping and sucking as they landed on her neck. He moved his hips against hers, and she felt herself getting wet from the friction of him getting hard against her panties, through his jeans. He lifted his sweater and took it off, and her hands quickly reached for the white t-shirt he was wearing underneath it. She took it off him and flung it somewhere, both of them not caring. She caressed his arms, his flexed muscles rippling.

Y/N’s cupped his jaw in one hand as she kissed him, the other moving down and rubbing against the seam of his jeans. She felt him growing hard against her hand and she moaned into the kiss.

“You’re sure, right?” he breathlessly asked, going for her neck again.

“Yeah” she gasped, closing her eyes. She quickly pushed him up and sat up, pulling her sweater off, pulling it over her head and off her arms.

Mark stared down at her light pink lacy bra and groaned. “Shit, baby.” He leaned in and kissed her, his hands in her Y/H/C hair.

Y/N started unbuckling his belt and pulled it through the loops, as he fumbled with taking his wallet out of his back pocket. He took out a foil packet and she took it from his hands. He unzipped his jeans and pulled them down along with his boxers, revealing his hard cock. He was a reasonable size, and she looked up into his eyes as she wrapped her hand around his shaft, pumping her hand slowly. She leaned back and laid down on the couch, biting her lip as she smiled up at him. He took the packet and tried opening it with one hand, but it fell out of his hand, disappearing somewhere on the couch.

“Oh shit” he whispered, laughing slightly.

“It’s okay, let me see where it is” she said, laughing along with him as she felt around for the foil packet. “If I don’t find it, I’ve started back on the pill, so we should be good.”

It was a moment or two before she found it, lodged under a couch cushion. She waved it with a smile and went to open the packet, but her eyes widened as she looked down at him. His hard on had gone down, becoming flaccid again, in the time that it had taken to find the condom.

Mark noticed her expression and looked down, cursing. “Oh shit, I-I-I uh,” he stuttered.

Y/N tried to calm him down, putting her hands on his shoulders. “It’s okay…”

“No, no, it’s not-” he shook his head, but stopped when she cupped his face, making her look at him.

“Mark” she said, shaking her head. “It’s honestly okay. It happens sometimes. It’s okay. Seriously.”

“Okay.” He nodded as he moved away from her, reached for his boxers and quickly put them on.

“Hey” she whispered, cupping his jaw. “I mean it.”

“Thanks.” He tried to smile but couldn’t. “I should go” he said, disappointed. He avoided her gaze, frowning. He quickly got up and got dressed again.

She walked up to him, wrapping her arms around his neck. “Look at me.”

He looked at her, still frowning. She leaned in, pecking his lips, softly.

“We’ll try again soon, and it’ll be amazing” she smiled, wagging her eyebrows. “Okay?”

His lips turned up in a small smile as he nodded. “Yeah.”

She kissed him again, a little harder this time, a way to emphasise what she just said.

“Get some sleep” she whispered against his lips. “I’ll see you on Friday, right?”

“Yeah” he said, as he moved away from her.

“Goodnight” she smiled.

“Goodnight” he said, as he picked up his coat and put it on. He walked over to the door and looked back at her. She smiled at him and blew him a kiss, trying to cheer him up.

“Bye” he called out.

She gave him a little wave as he walked through the door, closing it behind him.

Y/N’s mind was racing. Maybe what happened just now was because it hadn’t been very long in their relationship. Maybe they needed longer than 2 weeks to decide how they felt about each other and for the connection to form. It wasn’t his fault, and she knew that; it did happen sometimes.

They would try again. She was determined to try again because she did like him.

Or maybe she needed to stop trying to deny what she felt for the man who lived across the street. Would it be easier to end things with Mark now and move on with Dean? She shook her head, as she really thought it through. She couldn’t break Mark’s heart after what just happened, and Dean had just broken with Lisa recently. She kept coming back to the fact that he needed some time to himself.

She really wanted to make things work with Mark. Tonight didn’t turn out like she thought it would, but she couldn’t let it be a setback.

* * *

“So… Y/N” John said, smirking at his son as they walked back to their cars.

“Dad” Dean groaned, shaking his head.

“You failed to mention who she was, so clearly there’s something I’m missing” John smiled, as he dissected the situation.

“I don’t know what you’re talking about” Dean denied as they reached where the Impala and his dad’s truck were parked.

John chuckled as he turned to face his son. “You just denied it which means it’s serious.” John looked at him knowingly.

Dean shook his head as he looked at his father. “It’s nothing.”

Dean knew that admitting it wouldn’t change anything. She was still with _him_. It wouldn’t make a difference.

“Okay” John said, not believing him. “I’ll get it outta ya eventually. Or Sam will.”

Dean rolled his eyes. “Bye, dad.”

“Bye” John said, with another small chuckle.

They hugged and went their separate ways, with a promise from Dean that he’d be over during the week for dinner. As he drove home, his mind was on Y/N again. She was a constant thought and quite frankly, he didn’t think he could take it anymore. If his mind could stop teasing him with thoughts of her while he couldn’t do anything about it, it would make life more tolerable.

As he went to bed that night, he knew that it was too good to be true. He drifted to sleep, his thoughts morphing into dreams of Y/N and the life they could have together.

A life he desperately wanted with her but knew he couldn’t have.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	8. A Lesson in Acknowledging Feelings

**Summary for the Chapter:**

> It’s Y/N’s birthday dinner, which quickly takes a turn when Mark forgets himself and insults someone. Despite trying to cheer her up, Y/N begins to have her doubts about Mark after another chance to take things to another level, fails.

**Notes for the Chapter:**

> Warnings: Angst, Insecurities, Dean’s self deprecation rears it’s ugly head, Mark being an ass, Fighting, Making up, Smut: Handjob, Vaginal Fingering, Protected sex, Premature Ejaculation, Female Masturbation. 18+ ONLY. Fluff, Dean being sweet (yes, that’s a warning)

* * *

Friday brought not only Y/N’s birthday dinner later that night, but a full school day and Ben’s last day. Y/N stood to the side as she watched him hug all of his friends’ goodbye at the end of the day, her heart breaking a little as she saw a few of them wipe tears away. There were promises of visits in the future, catching up online and even playing video games. It was always hard to leave your school friends behind, and Y/N thought about how it wasn’t much different than when she left her home to come to Lawrence.

She smiled as she saw Ben walk over to her, a small gift in his hand. She smiled at him as she opened it, “World’s Best Teacher” printed in black letters on a white mug.

“I love it” she told him.

“Thanks for everything” he said, smiling.

“You’re so welcome. I know you’re going to do great” she smiled, lifting her hand. He high fived her. He picked up his bag and walked towards his mom’s car, Lisa leaning against it. As Ben said one last goodbye, Y/N took a deep, nervous breath as she saw Lisa walking towards her.

“Lisa.” She nodded as she steeled herself.

“I just want to say thank you for everything you’ve done for Ben” Lisa said, a small smile on her face.

“Well, he’s a good kid and I’m sure he’s going to do really well for the rest of 8th grade and into high school” Y/N said, a small smile on her face too.

Lisa nodded, looking like she wanted to say something else. “I just… I want to apologize. If I’ve ever been awful to you-” she said, but Y/N cut her off.

“It’s forgotten” Y/N said, simply. She wanted to let everything be in the past now that Lisa was starting over in her old hometown.

Lisa nodded, as she looked at Y/N. “He needs someone like you.”

Y/N blinked a couple of times, shaking her head. “I don’t-” Lisa smiled, causing her to stop what she was saying.

“Someone who’ll love him for exactly who he is and won’t try to change him into something he’s not” she explained, shaking her head.

They looked at each other for a few moments, before Lisa offered up her hand. Y/N took it, shaking it before letting go.

“Take care of yourself, Y/N” she said, as stepped back a couple of steps.

“You too” Y/N said, giving a nod as she watched Lisa turn and walk away.

She watched as she and Ben got into their car, and pulled away from the curb, driving away. Y/N hadn’t been expecting any kind of apology from Lisa, but at least it meant there was no ill will, and everyone could move on with a peaceful mind.

* * *

Y/N looked at herself in the bathroom mirror, as she pinned her Y/H/C hair back on the sides slightly, to be out of the way while she did her make-up. Charlie was next to her, using Y/N’s hair curler to fix her hair. Y/N’s “Badass Women” playlist was on in the background, Pat Benatar among others helping them to get ready for the night. She laughed as she watched Charlie trying to re-enact the moves from _Love Is a Battlefield_. Cas and Meg would pick them up soon to drive into the city for her birthday dinner.

“Dorothy’s coming to dinner straight from work. I’m really happy you’ll finally get to meet” Charlie smiled.

Y/N smiled too. “Me too. I’m excited to hear what she’s been up to in Chicago. What she can talk about, at least.”

Y/N went back to getting ready. She did her make-up, lighter this time than when the girls went out together; the night she met Mark. She put on her foundation, did a very light pink eye-shadow and winged liner, and a pink lip. She smoothed down her high-neck, long-sleeve top and made sure it was tucked into her leather mini-skirt properly. She went to her bed and sat down, lifting her leg to put on her black over-the-knee heeled boots, over her thigh-high stockings which disappeared under her skirt.

Charlie had just finished getting ready in a blue dress and brown boots, when they heard a car horn sound a few times. Y/N put on her silver dangly earrings, and then put on her long fawn coat. She picked up her small black bag as Charlie walked out first, and locked up her house. She and Charlie sat in the back of Cas’s car as he drove them into the city, through the drizzling rain.

Once they got to the restaurant and sat down, they all relaxed a little, thankful they made it in time. Dorothy arrived just as they sat down, coming in straight from work. As their first round of drinks came, Y/N frowned and looked down at her phone. Mark hadn’t called to say he was running late, which led her to conclude he was still working.

“Y/N, any word from Mark?” Meg asked, slightly concerned.

Y/N tapped her phone and didn’t see any notifications, as she shook her head. “No. He must be running late at work. He said he’d leave early, though.”

“It’s pretty bad out there, I made it here just in time before it started coming down” Dorothy said, looking outside the window at the rain.

“Well, hopefully he’ll be here soon” Charlie assured her, rubbing her hand up and down Y/N’s arm.

“Yeah” Y/N frowned, pressing the phone to her ear as she tried his number again.

Another thirty minutes passed with no word. She had called him and left a message when he didn’t pick up, plus sent him a few texts. She was about to give up and start thinking the worst, when Mark walked through the door, weaving around the tables with an umbrella and a bouquet of roses in one hand, and a small wrapped box in the other. Y/N got up with a smile and met him halfway, wrapping her arms around his neck and kissing him. Her heeled boots made her only an inch or two shorter than him. He was unfortunately still in his suit from work, but at least he looked good.

“These are because I’m late” Mark said, handing her the flowers. “This is because I adore you” he kissed her forehead, then handed her the gift. “And this is for your birthday.”

“Thank you.” She pecked his lips quickly before they came back to the table and sat down. She decided to ignore the fact that he got her roses, which she didn’t like. He didn’t know that yet and she didn’t want to hurt him by saying anything in that moment. Mark sat down on the other side of her, next to Meg. He quickly ordered a scotch and soda when a waiter walked by, before turning to the group.

“Well, it’s good to see everybody” Mark smiled, his arm automatically going around the back of Y/N’s chair, his hand caressing her arm.

Y/N opened her gift from Mark and gasped. It was a beautiful silver bracelet. “Oh Mark, it’s beautiful! Thank you!” she leaned in and kissed him, softly.

“I’m glad you like it” he smiled as he looked at her, fondly.

“I really do, but I said no presents.” She shook her head at him, opening the clasp of the bracelet. He took it from her as she offered her wrist. He put it around and closed the clasp.

He leaned in, his lips close to her ear, in a hushed tone. “Well, that’s what a boyfriend does.”

She looked up at him, smiling tentatively. “Boyfriend, huh?”

They hadn’t labelled anything yet and it still felt too soon, but maybe they were at that point and she just hadn’t realized.

“Yeah” Mark said, simply.

After a round of drinks, they ordered dinner. They mostly talked about work as Dorothy filled them in what she could talk about from an assignment in Chicago. Meg told some tales of the hospital, skipping the details as they were eating. Mark spoke of the ad agency and their latest campaign, and Y/N, Charlie and Cas told them how school was going. Once dinner was done and cleared, no one really felt like leaving.

“Should we head to a bar?” Charlie suggested.

“Yes, definitely” Mark laughed. “Y/N?”

Y/N thought about it for a second before smiling. “Fuck it, it’s my birthday weekend! Why the hell not?”

Cas laughed as she linked her arm with Meg’s. “We need to get her out of the school setting more often.”

Charlie nodded as she agreed with them, following behind everyone as they searched for a bar that had space for them.

* * *

They found a place that was playing good music and sat down in one of the quieter corners, that had leather couches and throw pillows. They all spread out on the three couches, but Cas got up to order them drinks. While he was at the bar, Y/N looked around, her head bopping to the music as she looked around the place. She liked the vibe, a very whiskey lounge feel, but with framed movie posters on the exposed brick wall and more than whiskey on the drinks menu.

As Y/N looked around, her eyes drifted over the bar in the centre of the room, with bar stools all around. On the far end, she noticed two men laughing about something. As one of them paid for their drinks, the other got up from his seat and put on his leather jacket. Her eyes widened as she noticed it was none other than Dean.

Dean looked around the bar as Sam paid for their drinks. This time. He had met him after work for a drink, something they did as often as they could on Friday’s, when Sam wasn’t too busy with case after case. He shrugged on his leather jacket, ready to head home and kick back with another beer and watch something on TV. He looked around the room, his eyes nearly falling out of their sockets as she saw Y/N looking back at him. What was she doing here?

“You okay, Dean?” Sam asked, having finished paying. He followed his brother’s line of sight and frowned. “Who is that?”

“Um… my-my neighbor, Y/N” Dean stuttered as he replied. He saw Y/N look away, distracting herself with conversation. Cas was there, so was Meg, Charlie, Dorothy and of course, Mark.

“You should go say hi” Sam said, jerking his head in that direction. “She knows Cas?” Sam asked, as he spotted their friend, as he put on his black coat over his charcoal suit.

“Yeah, she’s a teacher at the school” Dean said, looking at his brother.

Sam looked at Dean, narrowing his eyes. “What’s going on?”

“Nothing” Dean replied, too quickly as he glared at Sam.

“You’re such a liar” Sam chuckled. “Man, if I didn’t have to pick up food for dinner and get home before Eileen, I’d stay and get the full story.”

“Well, you better go before she gets back from work” Dean said, practically shoving Sam before he decided to stay.

“You should go over there, stay” Sam smiled, knowingly. “I want the full story soon, alright?”

“Would you just get, please?” Dean said, gesturing to the door.

Sam laughed as he shook his head, waving at Cas as he had looked up and had noticed them now. Sam quickly left, opening his umbrella as he walked down the path.

Cas waved Dean over, causing him to inwardly cringe. He really didn’t want to go over there but he knew he needed to. Were his friends swearing allegiance to Mark now? He needed to know more. He quickly ordered a whiskey, having stuck to beer with Sam knowing he had to drive back, but knowing he needed something stronger now. He walked over, watching Y/N shift on the couch, closer to Mark, who sat up a little, reaching his hand over.

“Good to see you again, man” he said, offering his hand.

Dean quickly shook it, making sure to let go quickly. “Yeah. So, what’s going on here?” He asked, looking at everyone before his eyes landed on Y/N.

“It’s my birthday dinner” she replied, smiling softly.

“Oh” Dean nodded, a small smile on his face. “Happy Birthday, Y/N.”

Y/N smiled in return. “Thanks. It’s actually on Sunday, but this one” she said, as she looked over at Charlie. “Had the genius idea that we should do dinner and drinks tonight.”

Dean sat down next to Cas.

“Yeah, she’s pretty smart alright” Dorothy laughed, looking at her girlfriend. Charlie rolled her eyes with laugh and gave her a quick kiss. Dean’s whiskey arrived at the table, and Mark sat forward.

“Alright” Mark got everyone’s attention as he picked up his drink and held it up for a toast. “Happy Birthday to Y/N, who’s about to be 28 years young.”

“Happy Birthday Y/N!” everyone called out as they raised their drinks, clinking their glasses together.

Y/N smiled as Mark leaned over and kissed her, softly. When she pulled away, she saw Dean looking at her and felt her heart sink. She hoped that she wasn’t flaunting her new relationship in his face, beginning to feel like crap, like she might be doing exactly that.

Dean hadn’t realized that’s how old Y/N was. He could see that she was younger than him, but by 7 years? He hadn’t thought it would be that much of a gap. What the hell was she doing kissing him, a guy so much older than her, when she could be with anyone her age? And she was. Or least Mark didn’t look much older than her, maybe a year or two. Dean scowled. She was really better off without him.

There was mostly small talk of the latest Marvel movie that had come out, and then how they hoped the Kansas City Chiefs would fair this season. Dean and Y/N’s eyes kept meeting during conversation amongst everyone, and they’d quickly look away at something else, trying not to bring attention to themselves. Dean felt his blood boiling as he saw Mark wrap his arm around her and them smiling at each other. At one point, as Dean thought he was discreetly looking at her, he caught Mark’s eye and knew that he had been caught. He gulped as he sipped his drink, hoping to a higher power that didn’t come back to bite him in the ass.

There was another round of drinks where they somehow got onto the topic of dream holidays. Dean felt like he couldn’t contribute to that considering the farthest place he had ever been was still within the U.S. He knew that he should’ve left a while ago, but somehow someone would keep the conversation going, and it was hard to find an exit point.

After that, they got back onto the topic of jobs when Mark realized he didn’t know anything about Dean. Y/N frowned when she noticed Mark sway a little as he sat up, knowing he had drunk too much and hoping he’d stop now.

“So, Dean” Mark sat forward, his arms leaning on his knees. “What do you do? I don’t even know.”

“I’m uh, I’m mechanic” Dean cleared his throat against the roughness from the alcohol. “It’s our family business. My grandmother was a teenager when her mother started it during WWII. Then my dad grew up there and started working there. Then me.”

“Wow” Mark nodded, but he scoffed a little. “Really?”

Dean eyebrows furrowed, wondering why he’d be confused by that. “Yeah.”

Mark hummed as he raised his eyebrows, taking a sip of his drink. “Didn’t you want to do more with your life?”

The silence that fell around their little corner was deafening. You could hear a pin drop despite low hum of other patrons in the bar and the music, and you could cut the tension with a chainsaw; the sound of it would’ve been welcomed at that point.

“Mark” Y/N hissed as she glared at him. She could feel the anger rising within her.

Dean gave him a tight smirk, jaw clenched as he looked down at the amber liquid in his glass. He looked up at Mark and pinned him with an unreadable expression. “And what’s that supposed to mean, exactly?”

Well, I just mean it’s kind of a limiting job, isn’t it?” Mark shrugged. “I know-” Mark started again but Y/N cut him off.

“Mark” she said, through gritted teeth. “That’s enough.”

Mark looked at her and his face fell. He quickly realized his mistake.

“Well, I’m pretty sure there’s absolutely nothing wrong with the path Dean’s taken” Charlie chimed in, glaring at Mark.

Dean looked at her with a small smile. He winked at her and then looked back down at his glass, downing the last of it like a shot.

“You don’t know me, Mark. I don’t give a fuck what you think about my life” Dean said, getting up from the couch. “I’m getting another drink.”

“I’ll come with you” Cas said, joining him as they both walked away.

Dorothy excused herself to the restroom, as Meg and Charlie and started whispering amongst themselves. No doubt talking about what just happened.

Y/N turned to Mark, absolutely fuming at this point. “How could you say something like that?”

Mark had realized that got a worse reaction than he thought and turned to her with apologetic eyes. “I didn’t mean for it to sound so bad.”

“If you knew him, you’d know how hard he’s worked to get where he is. You’d know that he has all of these amazing plans to expand and build the business even further” Y/N told him, defending Dean and his passion for what he does. His love for what he does.

Mark looked at her, a confused look on his face. “He’s told you all that? When?”

“It doesn’t matter when” she sneered. “He did tell me, yeah. He’s a good man and he doesn’t deserve what you just said to him.”

He rubbed his face, written with worry and guilt. “Fuck.”

“I think you better go over there and apologize” she said, still glaring at him.

He nodded but took her hand in his. “I’m sorry” he whispered, looking at her. “Please don’t be mad at me.”

She sighed and closed her eyes, her anger coming down to a simmer. “We’ll talk about it later.”

Mark nodded, looking like a kicked puppy. He picked up his drink and got up from the table, walking towards the bar where Dean and Cas had gone.

Charlie turned in her seat as Y/N turned to her friends.

“You okay?” she asked, rubbing her hand up and down Y/N’s arm.

“Yeah” she sighed, as she lifted her hand patted hers. “I just can’t believe he said that.”

“He’s had a bit to drink, maybe he can’t hold his tongue quite as well as others” Meg shrugged.

“Yeah, maybe” Y/N muttered, shaking her head as she looked down at the table.

Dean waited for the bartender to bring him a neat double of whiskey, as Cas stood beside him. He wasn’t ordering another as he still had to drive the girls back home.

“You alright, man?” he asked, patting Dean’s back.

“Yeah” Dean nodded. “He just doesn’t give me a good vibe, that’s all.”

Cas looked at his friend. Dean was almost never wrong about the vibes he’d get from people. He tapped Dean on the back as he saw Mark walk over. Dean turned around, sighing heavily as he saw him. Cas patted him on the back before he walked away, when he saw Meg waving at him to come back.

Dean really didn’t want to see him right now, but he also knew that Y/N probably had something to do with this, so he would have to. For her sake.

“Listen, Dean… I am so sorry, man. I didn’t mean to be such a jerk, I-I feel like crap” Mark apologized, looking scared.

As much as Dean wanted to take him because he was bigger than Mark and absolutely could, he wouldn’t do that to Y/N.

“We’re good” Dean nodded.

Mark sighed in relief. “Great.” He was about to walk away when Dean stopped him.

“Can I give you some advice?” Dean asked, jaw clenched as his gravelly voice was eerily calm.

“Sure.” Mark gave a small nod to continue.

“You can say whatever you want about me, I don’t give a shit.” Dean pinned him with a glare. “But you better make it up to her.” Dean looked over at Y/N. She was trying to smile as the girls were most likely distracting her, but it wasn’t reaching her eyes.

“Yeah” Mark sighed. “I think I’m in the doghouse.”

“Well, you did just ruin her night, so I’m pretty sure that’s not uncalled for” Dean sneered.

Mark shook his head, squinting at Dean but he didn’t say anything.

“Just…” Dean said, trailing off as he continued to look at Y/N. He turned to Mark and knew that despite his doubts, he had to trust that this guy would be good to her. “Take care of her. Okay?”

Dean drank the last drop of his drink and didn’t wait for Mark to say anything. He left his glass on the mahogany surface of the bar as he walked away. He heard Mark walking behind him, and once Dean turned, he saw Y/N hug him.

“Alright, we’re going to head out” Cas said, wrapping his arm around Meg. They both hugged Y/N as did Charlie and Dorothy, who were going with them.

“See you tomorrow night” Charlie told her. Y/N, Charlie and Meg had planned a girls’ night in, wanting to wake up on Sunday for Y/N’s birthday.

“Can’t wait” Y/N smiled, as she squished her friend in a hug.

She pulled away, seeing Dean put on his leather jacket. Dean looked at her, offering a small smile.

“Bye” he said, quietly to her.

“Bye.” Y/N had only just managed to get that out as he walked away towards the exit.

“Are you going to be okay to drive?” Cas asked Dean. Dean knew that it was more than just about driving home, though.

“Yeah, didn’t have a lot with Sam. I’m good” Dean nodded.

“Okay” Cas said, as they hugged, tapping Dean on the back a few times and pulled away.

Everyone went their separate ways with promises to catch up soon.

As Dean drove home, he thought about what had happened at the bar. He loved what he did for a living and he was proud of what he had achieved. It just pissed him off that Mark assumed he knew his life. He really gave off a weird vibe and he really hoped that Y/N would be safe with him. She had already been with one asshole. She didn’t need another.

* * *

Y/N walked into Mark’s apartment, dropping her bag on the kitchen bench along with her flowers, and hanging her coat on one of the high stools at the kitchen bench. She looked around the studio apartment, with its big windows that gave a great view of the city around them, clean industrial lines and steel applications in the kitchen. She turned to face him with a look of sadness mixed with raging anger. He shut the door and turned to her, still sporting that kicked puppy look, as he took off his suit jacket and hung it over the back of another kitchen bench stool.

“I’m so sorry I ruined your night, baby” he bemoaned, standing in front of her now. “I promise I’ll make it up to you.”

“Just promise me that you’ll never talk to people like that again” she said, firmly. “I mean it, Mark.”

“I promise, honey. I do. I really do” he stammered, trying to reach out for her hand.

“I really do mean it, Mark. I hate seeing people being put down for the things that make them happy. I won’t stand for it” she repeated her meaning, sternly.

“I promise, Y/N. I swear it” he pleaded, his hand still out.

She eyed him, really looking at him to see if he was telling the truth. He seemed genuine enough even though there was still a bit of doubt in her mind, but she had to take a chance.

She offered her hand, smiling slightly. “Okay.”

He took her hand in his and brought it to his lips, pressing a kiss to her knuckles. Her smile got a little bigger at that, as he pulled her in.

“Let me make it up to you now” he said, taking out his phone. He pressed a few things and suddenly music started to play within the apartment.

“You’re cheesy as hell, Mark Jenkins” she snorted. He was far too charming and managed to somehow get her out of her mood, which she was grateful for, as he tried to salvage this night for her.

“Oh, you love it, Y/N Y/L/N” he smirked, as he wrapped his arms around her and pulled her closer.

_Watching every motion_

_In my foolish lover’s game_

_On this endless ocean_

_Finally lovers know no shame_

_Turning and returning_

_To some secret place inside_

_Watching in slow motion_

_As you turn around and say_

_Take my breath away_

Y/N wrapped her arms around Mark’s neck, pushing herself closer to him as they kissed, heatedly. Soon, all of their clothes were being thrown off and around the room as they kissed. She reached out and took his length in her hand, stroking him as he leaned down and nipped at her breasts through her light blue, lacy bra. His hand came down and rubbed the outside of her matching panties, and she felt herself growing wetter as he continued to touch her.

“Fuck, that feels good” Mark groaned, as her hand continued to pump him, her wrist twisting every time it moved up over the head. It prompted him to hook his fingers in her panties and move them to one side of her inner thigh. He rubbed his fingers against her pussy, feeling how wet and warm she was. His thumb circled her clit as two of his fingers slipped inside her, moving in and out, causing her to throw her head back.

“Mark” she moaned as she looked up at him.

Mark lifted her up and carried her across the large studio apartment, gently dropping her on the bed. He reached for her thigh high stockings and pulled them off one at a time, before pulling her panties down her legs and throwing them over his shoulder. She pushed herself back to rest her head on the pillow, as Mark opened the drawer of his nightstand, taking out a foil packet. Y/N gulped, slightly nervous as she remembered how things went the last time they got to this stage. She pushed the thoughts away, as Mark opened the packet and rolled the condom onto his hard length.

Mark held himself up on his hands, as Y/N wrapped her arms around his neck. He leaned down and kissed her, as he guided his shaft to her entrance. He pushed into her slowly, until he was buried inside her. She sighed at the feeling of him, looking up at him with hooded eyes. He pulled back slowly, before pushing in again. Her hips met his, signalling to speed up. He began thrusting a little faster, causing her to moan. His eyes fluttered closed as he continued to move inside her.

“That good?” he asked, biting his lip.

“Yeah” she moaned. “Keep going.”

“Fuck, you feel so good, baby” he groaned, as his thrusts started to become faster.

Y/N frowned a little, as she looked down to see him moving faster.

“Mark, wait-” she said, but was cut off by his loud grunt.

“Fuck! I’m gonna cum!” he called out, his hips bucking into hers.

He thrust into her one last time and groaned again, as his release filled the condom. His eyes were still closed as he rolled off her and onto the bed, breathing heavily. Y/N eyed him with wide eyes, not being able to believe what just happened. He came. After 10 seconds.

“That was amazing” he muttered, a grin on his face.

 _Maybe for you_ she thought to herself.

Mark opened his eyes and took the condom off. He threw it in the trashcan next to the nightstand and cleaned himself with tissues. He turned back to her with the same grin, leaning his head on his hand.

“You came, right?” he asked, his other hand running up her body, cupping her breast over her bra.

She didn’t know what to say. She didn’t want to hurt his feelings and say “no, because you finished before we even really started”. Did he really think she had? If he had to ask, that means she didn’t. Clearly he didn’t know that.

She smiled up at him. “Yeah.”

“Good” he smiled, as he leaned in and pecked her lips.

Mark got up from the bed and she watched his naked form walk into the kitchen to get some water. She felt horrible for lying, but she wasn’t going to hurt his feelings and bring it up just after sex. Well, lack of sex for her. She sat up on the bed and found her panties on the floor. She picked them up and put them back on, and then put on her thigh high stockings. She got up and started searching around for her clothes. Mark watched her and raised an eyebrow as she started getting dressed.

“You’re leaving already?” he asked.

She fixed her skirt into place, as she tucked her shirt back in. She looked back at him and smiled. “Yeah. I should really go. The girls coming over tomorrow, and I want to clean the house before they do.”

“Okay.” He nodded, slightly disappointed. “I’ll call you Sunday” he promised.

“Looking forward to it” she whispered against his lips.

She pecked him once again and moved away. She slipped her boots back on and walked over to the bar stool to pick up her things.

With one last look at Mark, she blew him a kiss and then walked out of the apartment. In the Uber back home, as she stared down at the roses in her lap, she lamented to herself about how familiar the disappointment she was feeling in that moment was to the last time she and Mark tried to sleep together. Before he couldn’t keep it up, and now he couldn’t last a little longer. She thought about how maybe it was the alcohol. Maybe he was tried from work, but it didn’t seem like he was. Maybe if they tried again, he would be fine. She shook her head as she lifed it to stare out the window, rain droplets rolling down the surface.

Maybe it was her fault. Her past insecurities started to circle around her mind, as she came to the conclusion that maybe he wasn’t attracted to her. He kissed her like he was and touched her like he was, but maybe when it came down to sex, she just didn’t cut it. If he couldn’t keep an erection and now, he couldn’t hold back his release for a little longer, then maybe he was trying to rush everything because he couldn’t stand to be near her.

She really hoped that wasn’t it and it was just the evils of her past emotional abuse popping up again to play mind tricks with her.

Later that night, she was in bed and staring up at the ceiling. Having been left completely unsatisfied with her sexual encounter, she was now incredibly frustrated. A thought came to her as she turned on her side and opened her bottom drawer. She reached in and took out the item she was looking for, placing in on the bed next to her as she turned onto her back. She closed her eyes, as her hand moved down to her breast, her nipples straining against the fabric of her oversized sleep shirt. She rolled the nub between her thumb and forefinger, biting her lip as she began to feel her walls clench from what she was feeling. Her hand moved down under the covers and pulled the bottom of her sleep shirt up. She began to rub her fingers over her panties, feeling her arousal begin to wet the fabric.

Her mind conjured up images of her boyfriend, images that morphed into fantasies of them ripping each other’s clothes off, as his hips moved against hers, her head falling back against the pillows. She quickly moved her panties down her legs, kicking them off her feet as her hand reached for the pink stimulator. Turning it onto the first setting, she held the mouth of it to the bundle of nerves, instantly feeling the vibration run through her body.

She moaned loudly; knowing that no one would hear her in her own house was freeing, allowing her to be as responsive to her own pleasure as she wanted. She felt the wetness between her legs grow. The image of them locked in passion suddenly changed. Instead of Mark, she was seeing Dean on top of her. He looked so goddamn gorgeous and he was making noises come out of her that she wished he could do in real life. Her moans became louder. The vibrations continued to stimulate her clit, bringing her closer to her release.

“Dean!” The loud cry of his name left her lips, as the coil snapped and she came, her arousal slicking her inner thighs.

She smiled as the dream faded and her eyes opened, her breathing deep and heavy as she came down from her high.

As Y/N stared up at the ceiling, her breath settled back into a steady beat. The clouds of sexual fantasies in her mind cleared. However, as they did, nothing had changed. She could still see his beautiful face smiling at her, still feel his muscles against her hands. Like it had all been real.

She found herself wishing that it was, and not feeling guilty at all that it wasn’t her boyfriend she had been thinking of.

* * *

The next morning, Dean stood outside on his porch, waiting as Lisa and Ben picked a few last-minute things from the house. When Ben walked out, Dean gave him a small smile, but the kid could barely look at him, glancing away as he walked down the porch stairs. It was killing Dean to know how unhappy Ben was, but at the end of the day, the kid would’ve suffered if he and Lisa had stayed together. Dean wished he had realized that sooner, but at least Ben was still a little young to understand adult problems.

Lisa walked out of the house and down to the car, putting some things in the trunk and making sure the trailer was secure. Dean walked up to Ben, putting his hand on his shoulder.

“You take care of your mom, okay?” Dean asked, as Ben looked up at him.

He gave a little eye roll but nodded. “Yeah.”

“Here.” Dean took out an envelope from the back pocket of his jeans and handed it over to Ben. “This is for you, use it for whatever games you wanna buy, okay?”

Ben’s eyes widened as he opened the envelope. “I can’t-”

“You can, just don’t tell your mom until you have to” Dean winked at him and helped Ben stash it in his backpack. Once he dropped his bag in the car, Ben launched himself at Dean, hugging him.

“Make good choices” Dean said as he hugged him.

“I will” Ben nodded.

He pulled away and looked up at Dean one last time. Dean never thought he would ever even feel like a father figure let alone a father, but with Ben he got to experience it for a few years. He was going to miss this kid grow up but he knew that he made the right decision. For everyone.

Ben sat in the car and waited for his mother. Lisa walked over to Dean, her hands in her back pockets.

“All set?” he asked, as if she was just an acquaintance, and not someone he had spent the last 3 years with. That’s how it felt now.

“Yeah” she said, quietly. “Dean, I’m so, so sorry.”

This was about the hundredth apology he had gotten from her since the night they called it quits. He knew she felt bad and so did he by the end of it after what happened with Y/N, but the time for apologies was done. It was time to move on.

“It’s okay.” Dean leaned forward, and for one last time, he planted a kiss on her head. “Take care of yourself, Lisa.”

“You too, Dean” she said, her eyes looking misty as she looked up at him.

Dean watched as they drove away, feeling lighter than he ever had in 3 years. It dawned on him that he was alone now. It scared him but maybe he needed some time before he found himself in another relationship. Maybe that’s what Y/N was doing with Mark, too.

They would find their way to each other. They both just needed a little time.

Dean picked up his keys from inside and got into the Impala, driving into the main town square. It was Y/N’s birthday tomorrow and he needed to pick up something specific for her. He just hoped he could find it.

* * *

Y/N wiggled her fingers as she admired the fresh, dark lavender nail polish on her nails. The girls had come over to stay the night for her birthday the next day, and Charlie had insisted on doing her nails. They all sat at the dining table, an extensive range of polishes in front of them.

“Are we good with ordering Chinese tonight?” Y/N asked, in between blowing on her nails.

“Definitely” Charlie replied, a look of pure concentration on her face as she painted Y/N’s nails.

“Absolutely” Meg replied too, as she painted her own in black nail polish.

“Awesome.” Y/N shifted in her seat to move her other hand in front of Charlie.

“So, how was last night?” Meg asked. “Did everything go okay after we left?”

“Yeah, we talked. He apologized, I told him he couldn’t say stuff like that again. He was pretty remorseful, and I know he had drunk a lot, so I forgave him. I know he won’t do it again” she replied, a little too confidently.

Meg frowned, slightly as she looked between Y/N and her nails. “I sure hope so.”

“He won’t, Meg” Y/N promised.

“He better not” Charlie said, her tone quite angry.

Y/N sighed and looked at her redheaded friend. “How’s Dean?”

“He’s fine, really. He never lets this kind of stuff get to him” Charlie replied, looking up at Y/N from her nails. “I just don’t get a good vibe from Mark.”

“What?” Y/N asked, confused as she shook her head.

Meg and Charlie looked at each other, and Meg shrugged. Charlie looked at Y/N. “Are you sure he’s a good guy? Like… actually good? Not just putting on a show to impress everyone?”

Y/N bit her lip, not knowing to respond. She had started having her doubts after the incident last night, and knowing her friends were feeling the same didn’t bode well.

Meg looked at her and decided that they needed to steer away from this. It was best for Y/N to make her own mind up about this.

“So, after that…” Meg changed the subject with a smirk on her face. “Did… anything fun happen?”

Y/N gulped, her eyes shifting back and forth as she tried to come up with something to say. “Um… yeah. I mean, we-we um-”

“You what? Spit it out, Y/N” she said, her smirk getting wider.

“Did you guys do it?” Charlie asked, curiously.

Y/N huffed a laugh. “Yes.”

“And?” Meg asked, confused.

“And…” Y/N started, watching her friends listening intently. “He came. After ten seconds.”

Both Charlie and Meg’s eyes were blown wide as their mouths fell open.

“Ten seconds?” Meg asked, still shocked.

“Give or take” Y/N replied.

“Y/N…” Meg shook her head, not knowing what to say.

“He was probably just tired from work or he drank too much at the bar. I can’t base what he’s like in bed on this experience” Y/N explained, looking between her friends.

“Yeah, don’t look at me for this one. Sorry” Charlie stated, putting her hands up, as she got up to get herself a drink from the fridge.

“No, you definitely can’t. You just have to try again, when you know he won’t be so tired, and he hasn’t had so much to drink” Meg said, completely straightforward.

Y/N sighed in relief. “So… this is happened with you before?”

Meg smirked a little. “Well, not with Cas, but with other guys before him… yeah. Once or twice.”

“Okay” Y/N nodded. “This has never been an issue with anyone. I mean, bad sex in general, yeah… but never this.”

“Yeah, it can pretty awkward” Meg agreed. She frowned when it looked like Y/N was holding something back. “What?”

“We tried once before… last week and… he couldn’t keep it up” Y/N said, frowning.

“Fuck” was all Meg could say.

Y/N laughed bitterly, shaking her head. “Yeah.”

“Okay… I’m gonna be really honest here” Meg said, turning to Y/N. “You need to make sure this is genuine. Not just that you want this, but he wants this, too. If he’s serious about you, then you guys can talk about it and try again and put in the work.”

“You’re right” Y/N nodded, a new determination in her.

As the girls carried on with their girls’ night in, ordering Chinese food and watching their favorite rom-coms, Y/N felt better with what happened with Mark. Talking to Meg had cleared her of any insecurities she had when she was coming home after it happened. She had a feeling that things would be okay if they talked and tried again.

* * *

“Happy Birthday to you! Happy Birthday to you! Happy Birthday, dear Y/N! Happy Birthday to you!” Meg and Charlie sang at the top of their lungs as they burst into her room the next morning.

Y/N groaned but laughed as she woke up, sitting up in bed as she rubbed her eyes. The girls dragged her out of bed as she grabbed her fluffy robe and walked out to the living area with them. They had birthday cupcakes for her, which Charlie revealed she went and got from her place after buying them the previous day. There were some balloons and confetti on the table, and also coffee to go with their cupcakes.

“I love you both so much” she said, hugging them before they all sat down and enjoyed the little desserts for breakfast.

They had a great time continuing to chat about anything and everything. Y/N smiled as she realized how lucky she was to have these amazing women in her life. They had both helped her through a lot, some of it from her past with Ethan, and some of it from her present with Dean and now Mark. She missed her family, but she was beginning to feel like she had one in Lawrence, too.

Once the girls left after insisting on cleaning up their mess, Y/N got phone calls from her parents, her sister and brother-in-law and the kids, Katie and lastly, Mark. She was feeling the love from everyone and she couldn’t believe how happy she was. This time last year was a challenging time for her, getting over her break-up and going to therapy. Now she was in the best place she had ever been. There still some hurdles to face, but she knew those would work out the way they needed to.

As the sun began to set on her birthday, Y/N sat down and relaxed, saving her task of grading papers for her free period and lunch at school the next day. Just as she sat down to enjoy Chinese take-out leftovers and a FRIENDS re-run marathon, her phone chimed with a message. She picked up her phone and looked at the screen. Her eyes widened and her heart began to beat rapidly as she saw who it was from.

**Dean:** _Happy Birthday, Y/N. Check your front door. You can make your dad jealous now ;)_

Y/N frowned, shaking her head with confusion. She got up and walked over to the door. When she opened it, she looked around to see no one outside. Shaking her head, she was about to close the door when something on her doormat caught her eye. A large flat square badly wrapped in silver wrapping laid on the mat. She picked it up and walked back into the house, closing the door. She frantically unwrapped the gift, desperate to see what it was. She gasped as she stared down at the gift. She smiled as her eyes glistened.

It was a record. The Led Zeppelin II record she told him she still didn’t have, when she was at his house for dinner. He remembered something she just mentioned, just in conversation. He actually remembered.

She hugged the record close to her chest. She shook her head as she thought about him, and the thoughtfulness of this gift. He knew she loved the band, almost as much as he did, and he went out of his way to get her this.

How the hell was she supposed to move from him if he did things like this for her?


	9. A Lesson in Who to Trust

**Summary for the Chapter:**

> Thanksgiving time has Dean wondering whether Y/N is better of without him, as she tries to find the right words to broach the subject of her love life with Mark. However, she soon learns the kind of person he is and seeks comfort from the only person who she can truly trust.

**Notes for the Chapter:**

> Warnings: Swearing, Angst, Insecurities, Dean’s self-deprecation rears its ugly head, Self hate, Emotional Abuse, Mentions of Y/N’s ex, Fighting, Mark gets slapped, More angst, Tears, Comfort, Fluff, Dean being sweet (yes, that’s a warning)

* * *

Y/N stood in front of the whiteboard, filled with the kids’ ideas and thoughts about the latest book they were covering in class, _To Kill A Mockingbird_. Given that it was the Wednesday before Thanksgiving and they had a half-day and then Friday with no school, she tried to get as much work done with them as possible. She could see they were all itching to leave as soon as the bell rang, so she was really trying to keep their attention. When she looked down at her watch and saw that there was only about five minutes left, she sighed.

“Alright, guys. Why don’t we stop there,” she said, turning back to the class. “I know I’m about to lose you all to the bell soon, anyway.”

They all giggled as they finished writing notes one by one.

“So, before you go… remember to read the last few chapters before Monday” she said, flicking through the novel. “I want us to fill that board up again, okay?”

There were nods and several “yes, Miss Y/L/N”.

“Good” she smiled. “I hope you guys have great Thanksgivings’ and stuff yourselves with Turkey.”

They all laughed, and she joined them. The bell rang loudly, and the kids all sprung up at the same time.

“One at a time through the door, guys!” she shook her head, amused as she’d told them that so many times.

Once they had all left, Y/N packed up her work and shoved everything into her oversized handbag. She picked up her fawn coat and put it on over black sweater, brown checked skirt and brown knee-high heeled boots. She wrapped her scarf around her neck and picked up her bag, walking out of the room after turning the light off and shutting the door. As she walked down the school halls, her heeled boots echoing on the floors, she heard someone calling out to her.

“Y/N!” Charlie called out as she reached her.

“Hey” Y/N smiled. “Ready for the long weekend?”

Charlie sighed in relief. “So ready. I can’t wait to be at Jody’s tomorrow for dinner!”

“Is she a good cook?” Y/N asked, as they walked into the staff room to collect their boxes from lunch.

“She’s the best!” Charlie exclaimed, smiling. “Oh, damn. I haven’t even asked you what your plans are! If you don’t have any, come to Jody’s. She honestly wouldn’t mind one more.”

Y/N laughed, slightly as they picked up what they needed to in the staff room and then walked out. “Thanks for the offer, but I’m actually going to Mark’s sister’s for Thanksgiving. He asked me last week if I wanted to come with him and I said yes.”

“Oh. Okay” Charlie muttered, frowning.

Y/N knew something was up. “What?”

“It’s just… after everything that happened at your birthday, are you sure this is what you want?” Charlie asked, shrugging. “I don’t want to put doubts in your head-”

“You’re not” Y/N said, turning to her. “Truth is… I kind of already have them.”

She had been on edge since that night after her dinner, where Mark had insulted Dean but then also how their night ended. She knew they needed to talk.

“Have you thought more about what to say to him about… you know?” Charlie asked, her eyes widening at the suggestion.

Y/N sighed. “I have. I just have to be honest with him, tell him that he needs to see someone.”

Charlie nodded as they walked over to their cars. After goodbyes and wishes for Thanksgiving, Y/N headed home. As she drove, she thought her and Mark’s relationship. They had now been together for 6 weeks, and things were going… okay. However, they still hadn’t attempted to have sex again, settling for heavy make-out sessions. She knew they needed to talk about what happened that night at his apartment. She was hoping that after things finished up at his sister’s Thanksgiving dinner, he’d invite her over to his apartment again and they could try to see what they could do about it.

She was still a bit weary after what he had said to Dean, but Mark had been on his best behavior since then, and she hoped that he would never do that again. He could be a little arrogant sometimes, but she called him out on it, and he was good about keeping it in control. That didn’t mean she wasn’t worried he’d say something awful again. If that happened, she knew she had to do the right thing and end it. She was giving him another chance to prove himself, so hopefully he wouldn’t screw it up.

* * *

Sam walked out of Dean’s house, carrying three chairs, stacked. He took the porch stairs slowly, as Dean did the same behind him, with his own stack of three chairs. They walked over to Sam’s car, putting them into the backseat, before he shut the door.

“You sure that’s all mom needs?” Dean asked.

Sam nodded, making sure the doors were secure. “Yeah, just the chairs. She’s got everything else under control, as always.”

“I don’t know how she does it” Dean shook his head, smiling. “Oh man, I can’t wait to eat!”

Sam scoffed a laugh, shaking his head at his elder brother. “Yeah, I bet you can’t.”

“Hey, no judging me on Thanksgiving, Sammy.” Dean gave him a pointed look, but he smiled slightly, as this was their brotherly banter once again.

Y/N fluffed her Y/H/C hair as she looked at herself in the mirror. She fixed the beige, red and green plaid scarf around her neck as she turned to check that her light grey sweater was properly tucked into the back of her emerald green pleated skirt. She reached under and made sure her nude thigh-high stockings were properly attached to the suspenders and garter belt. Slipping her feet into her nude high heels, she put on her fawn coat, picked up her bag and quickly left the house. She needed to get to Mark’s, and then he was driving them to his sister’s.

As she walked over to her car, she looked across the street and frowned. Dean was outside, talking to a tall man with shaggy brown hair, framed around his head and neck. She smiled as something occurred to her; Dean had said his brother was tall. That had to be Sam.

Dean’s eyes found Y/N’s house again and he suddenly saw that she was outside, standing next to her car. Their eyes met and he felt his heart hammer against his ribcage. He hadn’t seen her since the night of her birthday. She smiled tentatively, with a little wave.

“That’s her, right?” Sam asked, when he noticed Dean looking at her. He remembered her from that night at the bar.

“Y-Yeah, Y/N” Dean stammered, as he continued to look at her.

Sam looked at his brother, eying him suspiciously. He had seen that look on Dean’s face a few times before, including that night at the bar and he knew immediately what it meant. He would need the specifics now, after he left the bar and couldn’t actually meet this girl.

“Hey” Sam called out to her, quickly walking over.

“Sam, what’re you doing?” Dean hissed, trying to grab his jacket but missing. He quickly followed behind him, Sam’s long legs taking him across the street in just a few steps.

Y/N gulped nervously, as she saw the tall man approach her. “Hi.”

“I’m Dean’s brother, Sam” he said, as he offered his hand.

She took it, smiling immediately. “It’s great to finally meet you. Dean’s told me so much about you.”

Sam smiled back, before looking over at Dean teasingly. Dean glared at him, as he shook his head. “Really? I wish I could say the same.”

Y/N laughed a little awkwardly, as they pulled their hands away. “Anyway, it was good to finally put a face to the name, but I should really go.”

“Oh, of course” Sam said, as he stepped aside.

“I’m guessing you’re going over to Mark’s” Dean broke his silence as he turned to her. His expression was blank as he tried not to show what he was feeling. He knew Sam would ask him about it if he did.

“His sister’s” she specified. “They invited me.”

Dean nodded slowly but didn’t say anything. Sam looked between them, sensing something wasn’t right and quickly changing the mood.

“Well, Happy Thanksgiving, Y/N” he smiled at her.

“You too, Sam” she smiled as she looked at him, before looking back at Dean. “Happy Thanksgiving, Dean.”

“Happy Thanksgiving, Y/N” he said as he looked into her eyes.

Y/N looked away from him quickly, as she stepped up to her car and got in. The boys walked away from her yard and back to where they had been, as they watched her pull out of the driveway and drive down the street. Once she was out of the vicinity, Dean pushed Sam.

“Why the hell did you go over to her?” he asked, exasperated with his younger brother.

“I was just introducing myself to the mysterious woman across the street, that you failed to tell me about” Sam replied, as a smirk appeared on his face. “I can see why.”

Dean’s eyebrows furrowed as his jaw clenched. “What?”

Sam laughed. “Man, you’re so smitten, it’s hilarious you can’t see it.”

“You don’t what you’re talking about, Sammy” Dean growled, as he scrubbed his hand down his face and shook his head. He turned around and walked back into the house.

“Come on, Dean, I’m not an idiot” Sam said, following behind Dean. “I saw the looks between you two.”

“Sam” Dean groaned. “I’m not talking about this.”

As Dean looked at him, an almost pleading look to drop the subject, Sam realized what was going on.

“Oh wow” he whispered. “You’re falling in love with her.”

“You’re insane” Dean denied. It felt wrong coming out of his mouth, but he couldn’t acknowledge it. Not when he couldn’t do anything about it.

“No, I’m not” Sam said, clearly. He was quiet for a few moments before he walked closer to Dean. “Look, man. I don’t know what happened between the two of you, but something did. Clearly whatever is, it started a while ago, while you were still with Lisa.”

Dean glared at him. “How the fuck do you do that?”

Sam shook his head and ignored the question. “So… what’s going on?”

Dean looked at Sam and sighed, resigning himself to the fact that he had to tell his little brother. After he explained everything, Sam didn’t look angry about any of it, and smiled at Dean.

“If Y/N’s the one you want to be with… then Dean, you have to go for it. You gave Lisa three years, and it didn’t go anywhere. Maybe this is it this time” Sam said, smiling.

“God” Dean groaned, shaking his head. “Way to go all chick-flick on this, Sammy.”

“Dean, just listen to me, please” Sam begged. “That relationship… it was killing you. Y/N seems great-”

“I can’t, Sam” Dean said, cutting him off. “She’s with someone else.”

“Oh” Sam said, frowning.

“Yeah” Dean agreed.

Sam looked over at his brother, knowing that wasn’t the only thing he was thinking about.

“What’s going on?” Sam asked, knowingly.

Dean shook his head. Sam really needed to stop being a freaking mind reader. It was better to just say it and deal with it rather than have his brother pester him for the rest of the day.

“I just… she’s amazing” Dean said, leaning back against the back of the couch. “What is she gonna want with me?”

“Dean-” Sam started but Dean cut him off.

“I mean she’s younger than me, by like… 7 years. She’s so fucking smart, she’s absolutely beautiful, and she’s the nicest person I know. She’s been through some shit and she’s still a good person. So… what would she want with me?” Dean scoffed, as everything he was feeling came out.

Sam shook his head, seeing Dean’s self-hating attitude resurfacing. “Dean… you’re the best person I know. You’re hardworking, you care about people. I’m sure she sees that in you, from all the time you’ve spent together. You’ve been there for her, helped her settle into a new life here. Dean, you deserve to finally be happy. If it’s meant to be with Y/N, then it’ll happen. You just have to be patient. You have to stop thinking you don’t deserve happiness, Dean. Hell, you deserve it more than most people.”

Dean looked at Sam and just nodded, not saying anything else.

“So… I’ll see you soon” Sam said, knowing he should leave it there.

Dean was too much in his thoughts to notice that Sam had left. Everything he just said was all true. So then why couldn’t he see that in himself? He decided to get ready to go over to his parents’ and not think about it at that moment. He had a lot to think about, but he just wanted to enjoy Thanksgiving first.

* * *

Y/N put a forkful of turkey and yams in her mouth, chewing slowly. She smiled at Mark’s sister, Ashley who sat across from her. Things were a little awkward, giving that she had never met them until now, but at least she and her husband, Stephen were nice people. They were really excited to meet her when she stepped through the door and had been really great hosts that made her feel welcome.

“So, how long have you been teaching, Y/N?” Ashley asked.

Y/N swallowed before answering. “Nearly 3 and a half years. 1 year of substituting and then 2 years in a full-time job, back home, and nearly half a year here. So, still pretty green but I really love it.”

“That’s amazing” Ashley said, smiling.

“Where’s home?” Stephen asked, taking a sip of his wine.

“Rhinebeck, New York” Y/N replied, simply.

“Wow” Stephen laughed. “That’s a big move. Why the change?”

Y/N smiled tentatively, not knowing how to answer the question. She hadn’t told Mark about Ethan yet, and she certainly didn’t want to do it over Thanksgiving dinner at his family’s house.

“I just needed a change” she told him. “Being in one place your whole life… it gets a little boring after a while. Plus, I saw this opportunity and had to take it.”

“Well, it’s a good thing you did” Mark smiled, leaning in to kiss her cheek.

She smiled at him before they went back to eating.

After dinner, Stephen gave Y/N a tour of the house as Mark helped Ashley with the dishes. They washed the big dishes, while they put the plates and cutlery in the dishwasher. As they cleared up, Mark turned to his sister with a smile.

“So… what do you think?” he asked. He wanted her opinion on her Y/N.

“She’s really nice; pretty” Ashley replied, nodding as she washed a platter.

“I feel a ‘but’ coming” Mark said, rolling his eyes.

“But” she started as she looked at him. “I think you need the full story on why she left home.”

“Why?” he asked, confused, as he wiped the platter once she handed it to him.

“Look, I’m sure she’s a great girl. I just think you need to know her reasons for leaving and see whether she’s been genuine or not” she replied, turning the tap off and turning to him.

“Why would she not be?” Mark said, glaring at his sister. He was a little angry that she would insinuate something about Y/N.

“I’m not saying she isn’t; I’m just saying that you need the full story. That’s it. Take it or leave it” she whispered as Y/N and Stephen came back into the room.

“Ashley, I love your house” Y/N smiled, as she gestured around her.

“Thank you” Ashley smiled in return. “Alright, dessert time.”

Meanwhile at the Winchester house, their dinner was far louder with a lot more people. John sat at one end of the table, with Mary at the other. Around the table was Dean next to Mary, Ellen next to him, Jo next to her. On the other side was Sam next to Mary, Eileen next to him, and Bobby next to her who was visiting them in Lawrence from South Dakota until after Christmas.

“So, who’s starting with what they’re thankful for?” Mary asked, smiling as everyone filled up their plates.

Everyone went around the table, saying what they were thankful as they all ate. There were normal answers of thankful for family and thankful for the chance to all be together.

When it was Dean’s turn, he was nervous. He wanted to tell them all something, something he was excited about and he wanted them to know.

“Dean?” Mary said, gesturing for him to speak.

“Um, well… I’m thankful for dad” Dean started, as he glanced over at his father. John looked at Dean, confused, as Dean went on. “I’m thankful that you trusted me with the garage when you left it to me to run because uh… I found a new building lot a few minutes outside of town. We’re expanding and turning that location into a restoration site for classics.”

The whole table erupted in cheers, as everyone congratulated Dean. Mary leaned over and kissed his cheek, hugging him tightly. Dean saw John get up from his seat and stood up, as John walked over. He put his hands on Dean’s shoulders, smiling at him.

“I’m so proud of you” he said.

“Thanks dad” Dean said, smiling in return. They embraced each other, John patting Dean’s back as they hugged.

As they pulled away, John looked like he had tears in his eyes. “Listen, let’s talk later. There’s something I want to say to you.”

“Okay” Dean nodded, slightly concerned about his dad.

“That’s awesome, man. Let me look over the contract for the building before you sign, see if everything’s legit” Sam said, smiling as he was happy for his brother.

“Yeah, for sure” Dean agreed.

“Anything you need from me, son, you got it” Bobby said, from across the table.

“Thanks, Bobby” Dean nodded.

Dean couldn’t remember the last time he had been this happy. Everyone shared that with him, as they were proud of the steps he had taken to get here. He loved what he did, and he was excited to build on it and make it something really incredible.

After eating, a few others helped Mary clear up and put away the food. Jo and Ellen were putting food in the fridge, as Dean walked in. As he walked past them at the kitchen bench, he reached into one of the Tupperware containers and took a slice of Turkey, munching on it.

“Hey!” Jo protested. “That was my share of the turkey.”

“It’s all one bird, Harvelle” he mumbled around the slice in his mouth.

“You suck, Winchester” she muttered, glaring at him.

He chuckled as Mary shook her head at him, rolling her eyes playfully as he started helping her with the dishes. Mary looked over at him as he stacked the dishwasher, his demeanor different all of sudden from being fine just a few seconds ago. She sensed something was off.

“Everything okay?” she asked.

Dean nodded, not looking at her. “Yeah. Everything’s good.”

Mary wiped her hands on a dish cloth, as she walked closer to him. “How come I don’t believe you?”

“Mom” Dean shook his head, not really sure if he was in the mood for his mom’s intuition. He couldn’t tell her about Y/N just yet.

“Look, whatever it is… when you’re ready to talk, I’m here. Like I always am” she reassured him, placing her hands on his cheeks.

“Thanks, mom” he said, quietly. She moved in and they hugged, tightly.

When they let go of each other, Dean saw his father wave him over.

Dean followed John down into the basement, which was more of a den for John now. He walked past his desk and over to a little bar cart he had, pouring a double of whiskey into two tumblers. He walked over to Dean and handed one over but didn’t drink it yet.

“What I’m about to say, it’s been a long time coming but I need you to know this” John said, looking down at his glass before he looked up at his son.

“What is it, dad?” Dean asked, his jaw clenched out of fear that something was wrong.

“I’m sorry, Dean. I’m sorry for putting everything on you when I left after that big fight with your mom. I apologized to her and she forgave me, even if I felt like I didn’t deserve it. I… I never apologized to you, though. I should have. You were 24, just starting at the garage in a more responsible role, but I left everything on your shoulders when I should’ve been there to help you” John said, shaking his head as his eyes glistened.

Dean nodded, understanding him completely. He had always understood why his dad left, and always thought he didn’t need an apology for it. When Y/N told him that it was an important part in moving on, he had agreed. And now here he was, receiving an apology organically, without having to say anything to prompt it. It was like she knew, and it was another reason Dean was grateful to her. If only he could tell his father how important she was to this moment finally happening.

“Dad, I get it. I understand why you left, and yeah sure I was angry when you did… but I got it. I still do. You leaving made me more responsible, and when you did properly hand the garage over to me a few years after that, I was ready for it because of what had happened. So… despite it being a hard time for all of us, it happened for a reason” Dean told him.

“And now you’re expanding the business” John smiled. “I’m so proud of you, Dean.”

“Thanks” Dean smirked.

They clinked their glasses together. As Dean took a sip, he saw his dad still looking at him.

“Now, I just want you to be happy with everything else in your life” John said, looking at him knowingly.

“Dad, I’m not telling you about Y/N” Dean shot him down.

“Oh come on” John laughed. Dean knew what to say to make his father drop the subject.

“Okay, let me put it this way. If mom found out that you knew about Y/N before she did, what would she do?” Dean asked, smirking.

John’s eyes widened. “Okay, you got me there.”

Dean laughed but didn’t say anything, as they both headed upstairs again.

* * *

Mark opened the door to his apartment and let Y/N in as he closed the door. She took off her coat and hung it on the back of the stool, as she paced the apartment. Her mind had been reeling in the car on the drive back from his sister’s, and she knew she had to speak up about what she needed to, soon.

“Can I get you anything?” he asked, as he stood in the kitchen.

“No, I’m good” she replied, shaking her head.

“Are you okay?” he asked, knowing straight away that something was wrong. “You were really quiet in the car.”

She sighed, knowing this was it. She tried to smile but she couldn’t. “Mark, we need to talk.”

His face immediately morphed into a frown. “About what?”

“About this” she said, gesturing between them. “I think that we have to get some help, some advice on what to do.”

“Y/N, you’re not making any sense. Advice for what?” he asked, shaking his head in confusion, as he walked over to her.

“For what happened last time when tried to have sex” Y/N sighed, knowing she couldn’t be discreet anymore. “For the fact that you… um… arrived in about 10 seconds of getting started, give or take.”

“What?” Mark shook his head, still not understanding.

She was trying to put it as kindly as she could. She didn’t want to hurt him. “I think you should see someone and then we can try again. Maybe it’ll be better then.”

Mark scoffed a laugh as he stared at her. “What the fuck are you talking about? I-I… I don’t do that.”

Y/N frowned and sighed, as she walked over to him. “Mark, it’s okay. I’m not upset. I just want to see what we can do, and then get past this little hurdle.”

“Little hurdle?” Mark asked, his eyebrows raised. “The fact that you’re accusing me of having some kind of problem with my dick isn’t a little hurdle, Y/N.”

He was getting harsh and she needed to bring the situation down again.

“I’m not accusing you, Mark. I’m telling you the truth. You need to see that this is real and that it’s okay. There’s nothing wrong with finding out what’s wrong and us having a great sex life” she countered, trying to remain calm.

He laughed, bitterly and it made her feel sick. “So, now we have a bad sex life?”

“No, I’m saying we don’t have one at all. When you can’t keep it up one time and the next time you get off way too early and I don’t at all… there’s a problem” she replied, glaring at him.

“So, what… you didn’t cum?” he asked, his face morphing into a look of anger. He moved closer to her as he waited for an answer.

She stopped glaring at him as she shook her head. “No.”

“Then maybe you’re the problem” he snapped; his eyebrows furrowed.

“Excuse me?” She moved closer to him, as her eyes widened.

“Yeah, maybe you’re tired from opening your legs for some guy behind my back, that you can’t!” he yelled.

Y/N saw red as her hand lifted up and slapped him across his face, sending a resounding sound around the apartment. “You son of a bitch! I’m trying to help you and that’s what you have to say to me?!”

“I don’t need your help!” he yelled in her face, his eyes glowering as he shook her.

Y/N pushed him hard, his back hitting the wall behind him. He glared at her but made no attempt to move.

“Lose my number, you pathetic ass” she bit back. “I hope whoever comes after me is happy knowing you’re a selfish jerk who can’t see that he’s got a problem.”

Mark was frozen in his place, not being able to move. She quickly took that opportunity to pick up her coat and bag, marching across to the door. With one final glance at him, she opened the door of the apartment and stepped out, slamming it behind her.

Y/N raced down to her car, which was parked in one of the side streets. She got in and didn’t waste time, driving away from the curb quickly. As she drove home, her mind raced. How? How had she gotten herself into this mess again? First Ethan, now Mark. Was she some kind of bad luck attractor? Did she not deserve to have a decent man in her life? She had to thank a higher power that it wasn’t anything worse.

Flicking the radio on, she tried to drown out her anger. As the song changed to Lizzo’s Jerome, she couldn’t help but smile at how appropriate it was. She didn’t need Mark. She didn’t need a man who couldn’t grow up and recognize he had a problem. He was better off with someone else, someone who could handle his baggage.

However, as she felt her eyes welling up and hindering her vision, her mind was reverting back to what it was like when Ethan was in her life. It was telling her that she didn’t deserve to be with anyone. That she was destined to be alone.

She couldn’t wait to get home and let everything she was feeling out.

* * *

Dean got out of the Impala, stretching out his limbs. He had truly stuffed himself with the delicious food his mother had made and now he was ready to kick back and relax on the couch, before heading to bed. He was going to go do a little work on the new house the next day, so he knew he needed to be up early.

As he walked to the porch stairs, he frowned when he heard screeching tires approaching. He watched as Y/N’s car pulled harshly into her driveway, the engine cutting out. She got out of the car and slammed the door, but jerked back as something got stuck.

“Fuck!” she yelled, not caring how loud she was considering she was clearly in distress.

Dean didn’t hesitate, rushing over to her. He saw her trying to pull the strap of her bag from where it was stuck in the door.

“Hey, hey, Y/N, it’s okay” he said, as he approached her and put his hand gently on her shoulder. He saw her face and wondered what the hell was going on. He had never seen her that angry before. She was breathing heavily, her expression angry but on the verge of tears. He took the keys from her hands and unjammed the door, taking her bag out before locking the car.

“Thanks” she whispered, not being able to speak louder.

“It’s okay, sweetheart” he said, softly. “Come on.”

He lightly took her hand, relaxing when she didn’t flinch, and guided her to her house.

When they stepped in, Dean helped Y/N over to the couch. He gently sat her down but grimaced as he watched her, her breaths becoming short and worrying.

“Y/N, look at me” he said, gently. When she did, he saw tears start to roll down her cheeks.

“Why…” she struggled to breath as she shook her head. “Why does this keep happening?” she asked, her voice breaking.

The damn broke as she began to sob. She hunched over but Dean held her close, wrapping his arms around her. She leaned her head on his shoulder, as Dean held her against his chest, his chin on top of her head.

“Y/N, sweetheart, it’s okay. I’m here” he told her, comforting her. “I got you.”

She gripped his jacket tightly, her body shaking against his. “I-I…”

“It’s all gonna be okay, I’m here, sweetheart. I’m here” he whispered in her ear.

Dean just held her and rubbed her back, soothingly. When Y/N’s breathing had returned mostly to normal and she was only letting out small whimpers, she lifted herself off him. She slowly opened her eyes, looking into his green eyes.

“I’m sorry” she choked out, wiping her face roughly. She rolled her eyes, clearly annoyed at herself, but he hoped she didn’t think that way anymore.

Dean shook his head, offering her a small smile. “Don’t ever be sorry, sweetheart.”

“I… I…” she said, shaking her head.

“Let me get you some water” Dean said, slowly unwrapping himself from her.

He went into the kitchen and found her glasses cabinet, taking one out and filling it with water. He walked back over and handed her the water, watching as she drank slowly.

She wiped her mouth on her sweater sleeve and put the glass on the coffee table.

“Did he… did he do something to you?” he asked, looking into her eyes.

Y/N shook her head and saw his jaw clench, his expression angry and sad. “It was my fault, I shouldn’t have upset him.”

Dean shook his head, gently taking her hand in his. “I’m sure it’s not, Y/N.”

She waited a few moments to calm down before she spoke. “He’s clearly got issues in the bedroom, but he can’t acknowledge that and decided to blame me for it instead.”

Dean could feel a raging fire within himself, but he kept calm for her. All he wanted to do was find Mark and kick his ass into oblivion, but he knew Y/N would never tell him where he lived for that very reason.

“I sure know how to pick them” she laughed, and they suddenly turned into quiet sobs as she launched herself into him, wrapping her arms around him as she buried her face in his neck. Dean held her close, never wanting to let her go. They weren’t sure how long they stayed that way.

She pulled away first, slowly and looked up into his eyes again. “Don’t leave me tonight” she said, quietly. “Please? I… I don’t want to be alone.”

“You’re not alone.” Dean leaned forward, pressing his forehead against hers. “I’ll never leave you.”

After a few more minutes of holding each other close, they pulled away from each other. Y/N’s sadness suddenly escalated into anger, her face forming into a glare as she stood up. She walked over to her little bar, picked up a tumbler and poured a decent amount of whiskey into it. She took a large sip, not even hissing as it burned her throat when it went down. Dean watched silently, worried about what she was feeling and going through.

“Y/N…” he started but she cut him off.

“Fuck him” she snapped. She turned around and faced Dean, scowl still prominent. “Fuck him for making me think that his problems in the bedroom were my fault. Fuck. Him.”

Dean didn’t say anything, knowing she needed to let it all out. He raised an eyebrow as he wondered what Mark’s problems were, but he figured he really didn’t need to know. He had a feeling he was thinking the right thing, though.

“I was trying to help him” she said, shaking her head with a bitter scoff. “What did I do to fall into something like this again?” she asked, her eyes glistening again. “He’s exactly like Ethan, and somehow… I couldn’t see it. I fell for it again.”

She shook her head as it dropped down, her eyes closed as she tried to hold back her tears. Dean walked up to her, lifted her chin up with his finger, gently, until their eyes met.

“You didn’t do anything, Y/N. It’s them who should know they’ve got a good thing when it’s right in front of them. You’re too good for them. Some guy is gonna come along someday and see that how lucky he is to have you” he said, staring into her eyes.

Y/N didn’t say anything as she continued to look into his eyes. He said some guy, but that’s not what she wanted. She wanted him.

She nodded, a small smile gracing her face. “Thank you, Dean. You’re… I feel like I’ll never be able to thank you enough. I owe you so much.”

He smirked, shaking his head. “You don’t owe me anything, sweetheart.”

Y/N smiled before she looked up at the clock. It wasn’t all that late, just 9pm, but she was exhausted. Her body felt drained and she really wanted to turn in early.

“I should get changed” she said, looking away from him. “Do you want to go home and get changed?” she asked him, as she took in his attire.

Dean shook his head, as he looked at himself and then up at her. “No, it’s okay. I’ll just uh… I’ll sleep like this.”

“You sure?” she asked, frowning.

“I’m sure, Y/N” he replied, with a small chuckle.

She smiled, softly with a slow nod. “Okay.”

Y/N excused herself to go get changed into her red and black plaid pyjamas and loose, black t-shirt. As she walked out, she laughed a little as she saw Dean standing in her living room, looking over her books, records and DVDs.

“Dean, you can make yourself comfortable” she said, as she sat down on the couch, her legs tucked under her. “I don’t mind.”

Dean walked over as he took his jacket off, hanging it over the back of the couch. He sat down on the other end of the couch, a large gap between them.

“I don’t bite, either” she laughed as she looked at him.

Dean gave her a nod as he moved a little closer. Y/N wasn’t satisfied with that, so she moved in rest of the way, her body incredibly close to his. She leaned her head on his shoulder, giving him the ability to smell her strawberry shampoo. She turned on the TV and flicked through the channels, trying to land on something.

“Tell me something good” she said, as she kept flicking through the channels.

“Something good?” he questioned, wondering what he could tell her. He smirked as it came to him. “Well… I’m still yet to sign the contract because I want Sammy to look over it, but… I found a building for the restoration site.”

She gasped, her face erupting into a huge smile. “Dean, that’s wonderful news!”

Dean was glad to see her happy after what occurred today. He laughed a little as his arms wrapped around her, when she threw herself into him, wrapping her arms around his neck.

“I’m so happy for you” she said, quietly but he still heard her.

“Thanks, Y/N” he smirked, as they pulled away from each other.

She smiled at him but looked away back to the TV, to continue flicking through channels.

Dean smiled as he watched her. He never thought he’d have another person in his corner, other than his family. Lisa used to be happy for him when he’d do well, before things started to change for them. It was different with Y/N, though. She wasn’t just happy for him. She was genuinely excited and wanted to know about every aspect of his life and his work. He knew in that moment that he couldn’t let her go. He’d give her some time, considering she still had to sort out her situation with Mark, but after that… he was going to bite the bullet ask her out.

_Tell me somethin’, girl_

_Are you happy in this modern world?_

_Or do you need more?_

_Is there somethin’ else you’re searchin’ for?_

When Y/N finally settled on a channel playing re-runs of The Three Stooges, Dean looked at the screen with a big smirk on his face. She took that time to glance over at him from the corner of her eye. This man was unlike any she had ever encountered. He was different from the men she had dated in so many ways. He may have had a tough yet incredibly handsome exterior, but his generous, caring nature was what drew her towards him. She needed to give herself a little time to clear her head and her life of Mark, but then she was ready to pursue things with Dean. She had been ready for him for so long, but their timing had been all off. Now, there was nothing to come in between them.

Looking at him as he sat next to her, she knew she wanted him to always be right there, that close to her. She knew she was in love with him. How could she not be after he had done so much for her?

_Tell me something, boy_

_Aren’t you tired tryin’ to fill that void?_

_Or do you need more?_

_Ain’t it hard keeping it so hardcore?_

_I’m falling_

_In all the good times I find myself_

_Longing for change_

_And in the bad times I fear myself_

Later that night, Y/N stared up at the ceiling, unable to sleep. She picked up her phone from the nightstand and looked at the time. 11.30pm. She unlocked her phone and opened her messages, typing one out.

Dean stared up at the ceiling of Y/N’s living room, his hands behind his head. His mind was whirling with thoughts of her and everything that happened that night. How could anyone ever treat her the way they had? He swore to himself that if she ever gave him a chance, he’d spent every day making sure she knew how important she was to him. How much he cared about her. How much he loved her.

His eyes widened as the realization sunk in. He was in love with Y/N. It had hardly been enough time, but he guessed that didn’t matter. Not being able to be with her had only made his heart long for her more, and now here he was. In love with her. He needed to keep that one to myself for a while. The last thing he needed to do was scare her off.

His phone chimed and he picked it up from the coffee table, reading the message that popped up.

**Y/N:** _Are you awake?_

Dean smirked as he typed back.

**Dean:** _Yep, just staring at the ceiling_

**Y/N:** _Can you come in here?_

Dean smirk widened as he threw the blanket off himself and got up from the couch. He walked down the hallway, the wooden floorboards cold against his warm feet. He slowly pushed Y/N’s bedroom door open, smiling when he saw her sitting up against the headboard. She sat up on her knees, a nervous smile playing at her lips as he walked closer to the bed. She pushed the covers aside and held out her hand. He took it in his hand, slipping under the covers. He reached up and turned off the light, settling in next to her. Y/N moved closer, resting her head on his chest, her arm around his waist. Dean smiled as he wrapped his arm around her, bringing her in closer to him.

“Goodnight, Dean” she whispered, her lips pressing against his shirt-covered chest.

He leaned in and kissed her forehead, his lips lingering against her skin. “Goodnight, Y/N.”

Soon, they both drifted off to sleep, dreaming of their future together.

_I’m off the deep end, watch as I dive in_

_I’ll never meet the ground_

_Crash through the surface, where they can’t hurt us_

_We’re far from the shallow now_

* * *

The next morning, Y/N woke up alone, but felt that the empty space next to her was still warm. She smiled slightly as she saw a note on the pillow. She smiled even wider when she read it, her heart soaring.

**Mornin’ beautiful,**

**I didn’t have it in me to wake you up, but there’s some things I had to do this morning. I promise I’ll be back later, and we can hang out.**

**See ya tonight,**

**Dean**

She couldn’t keep the smile off her face as she walked into the kitchen and started brewing the coffee.

Y/N couldn’t believe how much had changed for her overnight.

She was going to be cautious and make sure to take care of own mental state first, but she suddenly couldn’t wait to see what her future held when it came to Dean.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	10. A Lesson in Love and Hope

**Summary for the Chapter:**

> As Christmas time approaches, Y/N and Dean are sad they can’t spend this time together as she goes home to New York for the holidays. However, their Christmas presents to each other prove that they have a future together.

**Notes for the Chapter:**

> Warnings: Slight angst, brief mention of reader’s exes, Dean’s self-deprecation rears its ugly head (slightly), Dean being sweet (yes, that’s a warning), Fluff (yes, it’s true, you read that correctly lol)

* * *

Y/N smiled as she watched the kids rushing out the front doors of the school. It was officially the end of the day and the start of the holidays. She pulled her coat a little tighter around herself, as she called out to some students to be careful on the sidewalk, as it had snowed overnight. It was December 22nd, and school had let out early. In a few short hours, she was flying out to New York to spend the holidays with her family. She was nervous about the weather and was praying that her flight wouldn’t be grounded. She was also nervous to be headed home but considering Ethan had made the permanent move to L.A. she doubted he would be there.

She went back into the school and quickly packed up her things. She said goodbye to all the teachers and to Chuck and walked out with Cas and Charlie.

“Alright, here” Charlie said, as she handed her a small present in the parking lot.

“Oh Charlie, thank you” Y/N smiled, as she took it and handed one over to her as well. Y/N opened the gift, smiling as she saw the earrings she wanted during a time when she and Charlie had gone shopping, but didn’t buy.

Charlie hugged her after opening hers, a beautiful scarf that had her favorite colors.

Cas and Y/N exchanged gifts too, a new tie, white with little books on it for him because “blue may be your color, but you can branch out” and a leather-bound journal for her.

“Merry Christmas” all three of them hugged and called out to each other before they drove home.

Y/N hurried to get home as she still had a few more things to pack before she left in the evening. She had messaged Mark a few days after the incident with him, telling him that it was really over and to never call her, ever again. So far, it seemed like he had gotten the message, having not tried to contact her at all in the last few weeks. She was incredibly thankful for that. She was also thankful that in that time, she and Dean had been hanging out a lot, too. It was all very innocent and simple, just watching movies and making dinner together, or ordering take-out if they didn’t feel like cooking, after they both finished work. After that first night when they slept in her bed, they hadn’t done more than that. She was beginning to wonder when Dean would ask her out, and whether she should just ask him. Though she knew that maybe they just needed a little more time.

When she got home, she unzipped her boots and walked around in socked feet. She picked her suitcase which was half packed already and put it on the bed. She started putting some clothes and shoes and other items that she would need, including a few last-minute presents for her nieces.

Once she was finally finished packing, Y/N got changed into the clothes she’d be wearing to travel. A loose, grey, high-neck sweater and dark grey scarf, black pants and her grey coat, and white sneakers to make it easier on her feet in the airport. She had her carry-on and check-in bags ready by the door, needing both for this trip as she had to carry so many presents with her. She couldn’t wait to see her family after so many months away from them.

* * *

Dean shrugged on a thicker plaid shirt, wrapped a scarf around his neck and then his brown leather jacket. He picked up the rectangle shaped present he had wrapped horribly (he had never been good at that) and opened the front door, leaving the house and closing it.

He walked down the porch steps and across the path in his front yard, where he had cleared the snow off to the sides. He walked across the street and down the path of Y/N’s yard, which he had cleared for her, walking up her porch steps. He stood in front of the door and let out a big breath, pushing the doorbell. He had her present in his hand and he wanted to give it to her at that very moment. He had enlisted Dorothy’s help in finding it for Y/N, after an idea popped into his head and he couldn’t get rid of it. Considering Dorothy had connections, she had managed to get him a decent price on it; it was expensive but at least it didn’t cost him an absolute fortune once she haggled the price down.

The door opened, and Y/N was shocked to see Dean standing there. She stood at the threshold and admired how adorable he looked all rugged up to protect himself from the cold.

“Hi” she smiled, softly.

“Hi” he smirked, walking in when she stepped aside. “You leaving soon?”

“Yeah, my cab should be here any minute” she said, shutting the door.

Dean nodded, as he handed the present over to her. “Here.”

“Oh, Dean” she smiled at him, as she took it from him. “I was going to leave yours at your door, but-” she stopped herself as she tucked the present under her arm, gesturing for him to wait and walked into her office.

Dean watched as she came back, carrying a large, thin, rectangular shape wrapped up in silver wrapping and a giant red ribbon, tied into a bow.

“This is for you” she smiled, handing it over to him. “But you can’t open it until midnight, after Christmas Eve is over.”

“Okay. Wow. Thanks” he said, looking over it and wondering what the hell it was. “You can’t open yours till then, either.”

“New York’s an hour ahead” she laughed.

“Doesn’t matter. We both open them on our midnight. Deal?” he asked, smirking.

“Deal” she nodded, with a smile.

“So… New York. I’m glad you’ll get to see your folks for the holidays” he said, his smirk fading away knowing that she’d be so far away. He was happy for her, though. She deserved to see her family after so many months away.

“I can’t wait” she beamed. “Just to see them all, hug and cuddle my little nieces, soak up the holiday spirit.”

“That’s great.” He smirked. Seeing her love for her family made him positive that his own would love her, and she would love them.

He looked down at the present in her hand and smirked. He really hoped that it would let her know what he felt for her. Y/N looked at the present she got him and hoped that he’d like it. It was something for his new building where he was going to have the restoration garage. It would look amazing in his office, there.

A car horn honking pulled them out of their thoughts, and Y/N glanced down at her watch. She looked up at him smiling brightly.

“Merry Christmas, Dean” she said.

“Merry Christmas, Y/N” he smirked.

She moved in and wrapped her arms around his neck. His automatically came around her waist, pulling her into the hug. They held each other for a moment, basking in each other’s touch, their eyes closed. They jumped apart as the car horn sounded again.

Y/N laughed as she gathered her things. “I’ll see you when I get back.”

“Yeah” he agreed. “Here, let me help.”

Dean placed his huge present outside on the porch as Y/N walked out and closed the door to her house, locking it securely. Dean walked down the porch steps, with her check-in suitcase, putting it in the trunk of the cab. Y/N walked down and opened the door to the backseat, as Dean took her carry-on and put that in the trunk as well. She waited for a moment, as Dean walked over to her after closing the trunk. She really wished she could stay back and spend time with him, but she had to see her family. She was really looking forward to it, but she couldn’t help but feel sad that she wouldn’t be with Dean.

He looked down at her, looking as beautiful as the day he first saw her. He hated that he wouldn’t get to see her over Christmas and New Years’, wishing that she could stay back, and they could spend the holidays together. He wished he could see the look on her face when she opened the present from him, but he would have to settle for hearing whether she liked it or not. He was really going to miss her. _Kiss her!_ He thought to himself as he continued to look at her. Before he could think twice, he leaned in, pressing his lips against hers, softly.

It didn’t take long for it to deepen, as Y/N wrapped her arms around his neck. She smiled into the kiss, as he pulled her closer, their lips moving against each other’s. They were finally in each other’s arms again. There was so much behind the kiss; a promise of more to come, a promise of their future together, a promise of things being better for both of them. Y/N was the one to pull away, regretfully, but she had a plane to catch.  
“I really have to go” she said, frowning as she looked up at him. “But um… it’s about time you did that” she said, biting her lip.

Dean groaned when he saw her do that. “Don’t, sweetheart, or I won’t let you get on that plane.”

She laughed as she stopped. “Bye.” She leaned in and pecked his lips.

“Bye” he said, returning her smile.

With one last glance at him, she got into the cab. Dean watched it drive away with a smile on his face. He suddenly couldn’t wait to see her again.

* * *

Y/N eyes scanned over the crowds at the airport, trying to spot her dad. She had shoved her way through baggage claim and picked up her check-in and was now trying to find her father through the throngs of people embracing each other, excited to get their holiday celebrations underway. By the time they had a quick lay-over in Atlanta and flew into New York, it was 8.30pm, which was the scheduled time, and she was incredibly thankful to whatever higher power there was that got her there. It was still a 2-hour drive to Rhinebeck, and her family would most likely be sleeping by the time she got home, but at least she’d see them properly in the morning.

As the crowd around her cleared, she spotted her father and beamed as he saw her too, waving frantically. She rushed over to him and launched herself into his arms, hugging him tightly. She felt tears prick her eyes as she laughed, happy to finally see him again.

“Oh sweetie, let me look at you” he said, pulling away from the hug and holding her at arms’ length. “You look different.” He eyed her, his brows knitted together.

“I’m still the same me, dad” she shrugged, laughing slightly.

“It’s so good to see you” he smiled, his eyes glistening. “Come on, let’s go.”

As they walked out of the airport, a bearded man with glasses was jamming “It’s Beginning to Look a Lot Like Christmas” on his guitar. His case was open in front of him, and Y/N quickly walked over, dropping a 20-dollar bill in.

“Thanks” he smiled. “Merry Christmas!”

“Merry Christmas!” she called back and then hurried over to her dad, who was wheeling her bags to the parking lot. She smiled as she walked beside him; Christmas was her favorite holiday, and it was already off to a great start.

The drive back home was filled with Y/N catching up on everything she had missed. Her dad told her that her mom was going crazy with excitement of her being there soon and was making sure everything was perfect. Y/N laughed; her mom didn’t need to do anything extra to make things special considering it always would be no matter what, but she wouldn’t be her mom if she didn’t.

When they arrived home, Y/N gasped as she saw the house decorated so beautifully. The lights and decorations on the house were as stunning as always, and she was glad she got to see them again. As they went in, Y/N laughed quietly to herself as saw her mother, fast asleep on one couch, and her brother-in-law asleep on the other. Her sister and the kids were most likely asleep upstairs.

“I’ll get them up, you go upstairs” her dad whispered. “Brian can carry that up.” He gestured to her large suitcase.

“Thanks, dad” she whispered, as she quietly walked up the stairs with her carry-on.

She walked to her old bedroom and flicked on the light. She laughed slightly as she saw it still hadn’t changed at all since before she left for college. All her Backstreet Boys and NSYNC posters were still up on one wall, her Led Zeppelin ones still up on the other. She really had an eclectic taste in music. She heard a soft knock on the door and turned, seeing her brother-in-law, Brian, walk in with her suitcase. She smiled as she walked over, hugging him tightly.

“Jill’s gonna freak in the morning. I tried waking her up but Evie’s practically sleeping on top of her” Brian said, laughing slightly.

“I’ll catch them in the morning” she said, folding her arms across her chest.

Brian nodded, smiling at her. “It’s good to have you home. Goodnight.”

“Goodnight” she said, watching him leave and shut the door behind him.

Y/N quickly got changed for bed and slipped under the covers. As she drifted off, she couldn’t wait to see everyone else in the morning.

It was great to be home.

* * *

“Auntie Y/N!” a little voice yelled as it barrelled through Y/N’s room and bounced up on the bed.

Y/N gasped and flinched as a little body flung itself over her. She relaxed when she realized where she was, and held her 5-year-old niece, Evie tighter.

“I’m so happy you’re here” she smiled down at Y/N.

“So am I, sweetie” Y/N smiled, rocking her side to side as she didn’t let go.

Y/N looked up at the door when she saw her sister standing against the doorframe, holding her 8-month-old niece, Mia on her hip.

“This one wants to say hi, too” Jill said, smiling.

Y/N got up from bed, Evie stuck to her leg as she walked over to her sister. She hugged her tight, feeling a few tears escape down her face.

“I missed you, so much” Y/N said, holding Jill tighter.

“I missed you too” Jill said, pulling away and smiling at her.

Y/N smiled as she saw the baby. She was so big now, having only been 4 months when she left for Lawrence. She reached for her, but little Mia scrunched her face up, squirming into her mother.

“This one needs to be fed, so you get cleaned up and come downstairs. Mom’s making breakfast” Jill said, kissing Y/N’s cheek and taking the girls out of the room.

Y/N quickly brushed her teeth and threw her robe on over her pyjamas. She raced down the stairs and into the kitchen, smiling when she saw her mom’s back as she stood at the stove.

“Mom” Y/N said, as she walked over.

Her mom turned around and nearly started crying on the spot. She rushed over and took Y/N in her arms, hugging her tight.

“Oh, I’m so glad you’re here” her mom said to her as she pulled away, wiping her eyes.

“Me too” Y/N smiled.

“Alright, the pancakes are almost done. So, sit down and help yourself, and everyone else will down soon” her mom said, gesturing to the table that was already set.

“Can’t I help with something?” Y/N asked, frowning.

“No, you just got here, honey. Relax, we’ll put you to work tomorrow” her mom laughed, as she playfully shoved her towards the dining table.

Y/N laughed and shook her head as she walked over, licking her lips at the sight of the delicious breakfast.

After a great breakfast with her family, Y/N helped Evie decorate another gingerbread house, because the two she did with grandma yesterday weren’t enough. Jill sat with Mia on her lap, across from Y/N at the dining table, as Let It Snow played in the background through the house. Brian had gone back to their house to get some more bottles for the baby, and her parents had rushed out to deliver some homemade Christmas cake to their friends. So, Y/N was glad she and her sister were alone for a while, to have some proper girl talk.

“So…” Jill trailed off, as she distracted the baby with her toy, and tried to ice a piece of the gingerbread house with one hand. “How are things with Mark?”

Y/N smiled, sheepishly, feeling guilty she hadn’t told her sister yet. “Things are… over.”

“What?” Jill asked, wide eyes looking up at her.

Y/N shrugged, as she iced one part of the roof for the gingerbread house. “Things got a little… complicated.”

“Well, considering I only know whatever you told me up to the third date, I need the specifics” Jill said, shifting Mia when she started to fuss.

“I know, I’m sorry I haven’t talked to you in a while” Y/N frowned, looking up at her sister.

“It’s okay, Y/N. Don’t apologize. I mean, we’ve both been busy” Jill laughed slightly, gesturing her head between her two daughters.

Y/N looked at Evie sitting next to her and smiled, seeing her niece in full concentration as she decorated, her tongue sticking out.

“This one has to leave, though” Y/N said, looking at Evie and then Jill.

Jill nodded in understanding. “Evie, honey. Can you stop what you’re doing for a second?”

“What is it, mommy?” Evie asked, her big eyes looking at her mom.

“Can you make sure all the presents are kept neatly under the tree?” Jill asked her in return.

“Okay” she replied, simply, not understanding why she had to go but doing it anyway.

Once she was out of earshot, Jill turned to Y/N. “Okay. Spill.”

Y/N took the next few moments to tell Jill everything that had happened with Mark.

“Fuck” Jill remarked, not knowing what to say.

“Yeah” Y/N nodded.

A short pause fell between them as Jill thought about everything her sister just told her.

“Why didn’t you say anything sooner?” Jill asked, her eyes teary.

“I didn’t want you guys to worry about me” Y/N replied, shaking her head. “And don’t tell mom and dad, they’d freak out. I’ll tell them myself at a later stage.”

Jill sighed, but nodded. “Okay.”

“Thank you” Y/N smiled, softly. She bit her lip, wondering if she should tell her sister about Dean too. Maybe it was too soon?

Jill tapped her fingers on the table as she watched her sister, her face looking like her brain was overloaded with thoughts.

“There’s something else” Jill said, knowingly. “Isn’t there?”

Y/N looked at her sister, tentatively. She wasn’t sure if she should say it or not.

Jill cocked her head to the side, a smile gracing her face as she understood. “Who is he?”

Y/N scoffed, impressed with her sister’s intuition.

She spent another couple of minutes telling Jill everything about Dean. She felt a smile tug at her lips as she talked about him. After everything she had been through in the past, and then with Mark, she thought for minute back there she’d never be able to think of dating someone again, but things were different with Dean.

“So… when you get back, what’s going to happen?” Jill asked, curious about what she was thinking of doing.

“I… don’t know, but… I know that he’s it now” Y/N replied, her smile growing.

Jill smiled. “I gotta say, I’ve never seen you like this. Yeah sure, you’ve been with a few guys, but this is different.”

“It feels different this time” Y/N nodded. “I don’t want to get my hopes up, but… it feels like this is it. And I know he’s some years older than me, but that doesn’t matter to me.”

Truth be told, men who were slightly older than her were a turn on for her. Plus, she had only ever been with guys her own age. Maybe it was time for a change.

In that moment, Y/N’s baby niece started to fuss in Jill’s lap.

“Oh, honey. You can’t be hungry, I just fed you” Jill said, frowning as she didn’t know what was wrong.

Y/N got up and walked over to their side of the table. She slowly picked up the baby and held her close, lightly bouncing her. Little Mia smiled and Jill smiled, too.

“She just needs a little lovin’ from her aunt” Y/N smiled, kissing her niece’s chubby cheek.

Jill admired her sister with the baby. “You look good like that.”

“Stop” Y/N laughed, shaking her head. She didn’t need those thoughts in her head at that moment. She had always loved children, and couldn’t wait to have her own, but she wondered if Dean was the one who she would have them with. Did he even want any?

The doorbell rang and interrupted them. Y/N gave little Mia back to Jill and walked to the front door. She screamed when she opened it and saw Katie smiling at her. The friends hugged tightly, laughing.

“I’m so glad you’re here!” Katie said, swaying them side to side.

“Me too” Y/N tearfully told her, letting go of her and letting her into the house. “You just missed girl talk, though.”

“Well, catch me up. I’m all ears” Katie said, walking into the house, taking off her coat.

Y/N laughed as she followed behind her, ready to divulge everything she told Jill to her best friend as well.

* * *

The next day brought a whirlwind of familial chaos, as Y/N’s family got everything ready for Christmas Eve dinner. Christmas carols were playing in the background, as her mom worked on the ham, her dad helped with all the sides and her sister was in charge of decorating the rest of the house, the table and setting it. Brian was keeping the kids entertained and Y/N was making pudding and few other treats for dessert.

It took all day, but they finally got everything ready and in time for dinner. As everyone got dressed and ready, Y/N took some time to admire the house. The lights were dimmed, the candles were lit, and everything was bathed in a beautiful glow. The lights on the tree were shining, and the fireplace crackled, adding to the ambience of the room. She was so glad to be here with her family and to spend this time with them.

_Have yourself a merry little Christmas,_

_Let your heart be light_

_From now on,_

_Our troubles will be out of sight_

She quickly had a shower, and then got ready for dinner in a red, A-line dress, with sleeves that came to her mid-forearm. She pinned her Y/H/C hair into a bun, a few strands framing her face. She put on her nude heels and then went downstairs to join her family.

Dinner was absolutely divine, and her mom had outdone herself, yet again. Everything from the ham to the pudding for dessert was perfect, and everyone was absolutely stuffed by the end. They all relaxed on the couch and sang some carols, drank eggnog and enjoyed the fact that they were all together again. For the first time in a long time, Y/N had no fear about Ethan or Mark, or any of the other troubles she had had in the past. All she needed was her family and hoped that the man who she had fallen in love from the minute she saw him, would also be a permanent figure in her life.

_Have yourself a merry little Christmas,_

_Make the Yule-tide gay,_

_From now on,_

_Our troubles will be miles away_

It was pretty much the same vibe over at the Winchesters.

Mary had assigned jobs for everyone, stating to the boys that they weren’t getting out of it just because they didn’t live at home anymore. She made Eileen and Sam come early as well as Dean, so that they could all do their assigned jobs.

Once everything was ready before dinner, everyone put on their ugly Christmas sweaters, a Winchester tradition that was something silly but fun. Bobby, Ellen and Jo arrived, and they all greeted each other. They sat around talking and laughing as they ate, and afterwards sat around on the couches, listening to carols while drinking eggnog. No one trusted Sam with it anymore, so it was Eileen’s job to mix it since she joined their family. Dean smiled as he looked around at his family, content for the first time in years.

_Here we are as in olden days,_

_Happy golden days of yore_

_Loving friends who are dear to us,_

_Gather near to us once more_

However, Dean was the first one to notice when Eileen wasn’t drinking any. He gestured to her and then signed “are you okay?”, which was just one of the things of what little he knew, but he was trying to get better at it. She nodded and then smiled at Sam. They had a small conversation between themselves, before Sam turned to everyone with a huge smile on his face.

“Well, now’s as good a time as any to tell you… we’re having a baby” he said, beaming. “Eileen’s 16 weeks in.”

Dean’s eyes widened but his smile grew as he got up, and hugged his brother first, Mary and Eileen hugging as Mary cried. Everyone hugged the expecting parents, before they all sat back down.

“Congratulations, guys” Dean said, as he returned to one side of the couch. “That’s awesome, seriously.”

Sam smiled as he kissed Eileen’s cheek. “Thanks, Dean.”

“Oh, I can’t wait for my first grandchild!” Mary exclaimed, as John kissed her head.

Dean’s mind wandered off as Eileen and Sam were talking about moving into a bigger place. Mary was listening intently, but Dean couldn’t focus on the conversation. He couldn’t have been happier for his little brother and sister-in-law. They were going to make great parents; he knew that to be the absolute truth. However, he couldn’t help but feel an unexpected sadness wash over him. He never thought of himself as the “having kids” type of guy, hell, he never pictured himself in a serious relationship. That was when he was younger though. As he got older, he realized he wanted those things, and even though he was happy for Sam, he felt a little jealous sometimes that his little brother would have all of that before he did.

The last year of his life had been a waste, as he tried to salvage a relationship with Lisa. He couldn’t help but think where he would be if he had broken up with her a year ago. _Mostly likely with Y/N as soon as she got to Lawrence_ he thought as he tried to concentrate on the conversation his family was having. It was no use though, as his mind continued torment him with the possibilities that could’ve been, if he had just claimed his freedom sooner.

Dean silently excused himself and walked out to the back porch of his childhood home. He let out a long breath, seeing it cloud up in the cold. He sipped the eggnog, feeling the kick of the alcohol warm him up. He smiled sadly as he thought about Y/N, so far away from him, in New York with her own family. He wondered what she wanted from life and whether their wants would align, whether having a family was something she wanted or not. He really hoped so.

“Merry freakin’ Christmas” he mumbled to himself. He never had a problem with being alone, but as he got older it had started to become a fear for him. Maybe that was why it took so long to see the whole truth with Lisa.

“Sure is” he heard someone say behind him. He turned and saw his mom standing behind him.

“I’ll be back in soon, mom” he said, turning away from her.

“Actually” she started as she stood next to him and faced him. “I was thinking we could talk.”

“About?” he asked, staring down at his eggnog.

Mary was quiet for a moment before she spoke. “Who is she?”

Dean scoffed as he closed his eyes. Of course his mom had figured it out.

He opened his eyes and looked at her, his jaw clenched. “She’s… she’s the best person I’ve ever known and… I have no idea if I should do anything about this because honestly, she deserves more than me.”

“Isn’t that up to her?” Mary asked, knowingly. “If you’re spending so much time with her, and I know you have because I’ve hardly seen you over the last few weeks, then doesn’t that mean that she wants to give you a chance?”

Dean blinked a few times as he took in what Mary just said. “I guess.”

“Then all you have to is take the leap” Mary smiled.

Dean nodded slowly, scrubbing a hand down his face. “Yeah.”

Mary nodded. “Just know, you have to bring her here because we need to meet her.”

Dean groaned and laughed, shaking his head. “Great.”

Mary smiled, leaning over to kiss his cold cheek. “Come inside soon, it’s way too cold.”

“I will” he promised as he watched her go back in.

Dean smirked as he thought about how Y/N would actually fit in with his family. He knew he needed to muster up the courage and just ask her out. Let go of the fear that had developed because of everything that had happened with Lisa. Maybe it was too soon after, but the truth was, he didn’t want more time. He was ready to be happy.

_Through the years_

_We all be together,_

_If the Fates allow_

_Hang a shining star upon the highest bough._

* * *

At midnight, Y/N and her family all wished each other a Merry Christmas, before they cleared everything up and each of them headed to bed. They would be up in several hours again, to open the presents anyway. As she went upstairs, there was one thing she needed to do before she headed to bed. Walking into her room, she shut the door and walked over to her carry-on bag. She opened it and found the present from Dean. She moved the bag back to the floor and then sat down on her bed, the present in her hand.

She laughed a little as she saw the envelope on it had her name but also “READ AFTER OPENING” in Dean’s all caps writing. She opened the wrapping, frowning when the thing was wrapped in brown paper as well. She unwrapped the brown paper, noticing that it was a very old but beautiful, hardcover book. She frowned again, but as she turned the book around and saw the spine, she gasped loudly.

In her hand, was an early edition of her favorite novel of all time, Jane Eyre. Y/N’s eyes widened as they started to well up with tears. She remembered telling him it was her favorite at dinner with him. It was yet another thing he remembered about her, the Led Zeppelin album being the first. She felt the tears rolling down her face as she opened the book, slowly flicking through it. She closed it and hugged it to her chest. She couldn’t believe he had done this for her.

She put the book in her lap and picked up the envelope, opening it and sliding the card out. Opening the card, she smiled through tears as she read his words.

**Merry Christmas, sweetheart.**

**I hate that you’re not here with me, but I can’t wait until you’re back. There’s a lot that I wanna say, but I’ve never been good with words. So, I’m just gonna do my best.**

**I’ve never been surer of anything, than I am that you’re the greatest person that I’ll ever know. You’re beautiful, smart, strong as all hell, and have the kindest heart of anyone I know. I know how freaking lucky I am that you’re in my life.**

**I hope this present lets you know how much you mean to me. How much you’ll always mean to me.**

**Y/N, this is it for me. You’re it for me. I need you to know that.**

**Have an amazing time with your family and I’ll see you as soon as you get back.**

**Dean**

She laughed through her tears, shaking her head. She had never been surer of anything either; that he was the greatest man she had ever known. That she was so madly in love with him, and she couldn’t wait to tell him that someday.

_And have yourself a merry little Christmas_

* * *

When it reached midnight in Kansas, Dean said a quick “Merry Christmas” to everyone, but everyone kept wondering why he was heading off so quickly.

“You know, you can just stay the night to open presents in the morning” Mary told him as she handed out warm cider to everybody.

“No, there’s uh… something I gotta do” Dean said, putting his jacket on.

“Something or… some _one_?” Jo asked, smiling suspiciously.

“Shut up, Jo” he groaned, glaring at her.

Jo laughed as she and Sam looked at each other.

“Seriously, what’s the rush, kid?” Bobby asked, curiously.

“Can a man not have a little time to himself anymore? Jeez” Dean grumbled, shaking his head.

“Alright, everyone leave him alone” Mary said, calming everyone down. “He’ll be back soon anyway.” She leaned in and kissed his cheek, patting his shoulder.

He would be back in several hours anyway to open presents with everyone, but at that moment he had to see what was awaiting him.

When he got home, he walked over to the big present from Y/N, resting against a wall in his living room. He chuckled as he looked over the size of it, wondering what the hell she had gotten him. He opened the large bow, letting it fall away. He dug his finger into the edge of the wrapping and ripped it open, at every side to see the present more clearly.

“Holy shit” he gasped as his mouth open in awe.

The present was a large black frame, with a black and white photo of his beloved Baby, shining away in the sun. It looked like his backyard in the background of it, and he had to wonder how she took this photo. On the corner of the frame was an envelope with his name written on it. He took it and opened it, smirking as he saw her handwriting.

**Merry Christmas, Dean!**

**I took this photo for you to hang in your new office at the restoration site. There’s nothing better to convince the customers to bring their cars to you than a picture of Baby.**

**I’m so proud of you for everything you’re working towards. It’s going to bring so many amazing things your way; don’t let anyone tell you otherwise.**

**I hope that the new year brings you everything you wish for, because if there’s anyone who deserves it, it’s you. You’ve been an amazing support to me, and I’ll never forget everything you’ve done for me. Ever.**

**I can’t wait to see you when I get back and just be near you again.**

**Y/N xx**

He smirked as he read over the note a few times. She really was something else. He couldn’t believe that someone like her would want someone like him, but he knew how lucky he was that she was in his life.

_And have yourself a merry little Christmas_

He looked at the clock and saw that it was ten past midnight, which meant it was ten past 1am in New York. Y/N was probably asleep, but he really wanted to speak to her. He sent her a quick text, asking if she was awake. When he got a reply instantly that she was, he dialled her number. In New York, Y/N sat up instantly when her phone rang and picked it up.

“Hi” she said, smiling. “Dean, I… I don’t even know what to say.”

“Did I make the English teacher speechless?” he teased with a smirk on his face.

“Yes” she admitted. “Dean, it’s… thank you. Thank you for everything you’ve done for me.”

Dean smiled. “Well, it’s like I’ve said before, sweetheart. You don’t ever have to thank me.”

“Did you… did you mean it? What you said?” she asked. She already knew it was the truth, but she just needed to hear it. She just needed to know for certain.

“Yes” he replied. There was no pause. No hesitation.

Y/N felt tears welling up in her eyes all over again. “You’re… you’re it for me, too.”

Dean smiled, feeling like his heart would burst from her confession that she felt the same.

“Thanks for the photo. It’s so freaking awesome, Y/N” he smirked as he looked over at it.

“You’re welcome” she said, smiling. “But Dean, now our presents are totally uneven. This would’ve been so expensive-” she said as she picked the book, but Dean cut her off.

“Hey, no. It’s not about that, okay? I knew… I knew that I wanted you to have it. Plus, with Dorothy’s help it wasn’t too expensive, so we’re good” he reassured her.

“Okay” she said, nodding.

Dean looked up at the time and knew he should end the call. “I should let you go. Merry Christmas, Y/N.”

“Merry Christmas, Dean” she smiled as they both hung up the phone.

That morning, as they fell asleep for a few more hours before they had to wake up again, even with miles and miles between them, they fell asleep with dreams of each other. They fell into a peaceful slumber, knowing this was the start of something magical for both of them.

_And have yourself a merry little Christmas now_

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	11. A Lesson in Moving Forward

**Summary for the Chapter:**

> New Year’s Eve night finds Dean and Y/N still separated, but it’s nothing a little fun over the phone can’t fix. After a visit to her therapist, Y/N returns to Lawrence to have an important conversation with Dean, before they can embark on their journey as a couple.

**Notes for the Chapter:**

> Warnings: Swearing, Smut: Phone sex, Dirty talk, Male masturbation/Hand job, Female masturbation/Vaginal fingering. 18+ ONLY. Therapy session, Insecurities, Self image/worth issues, Mentions of reader’s ex, Mention of physical altercation against reader, Dean’s self deprecation rears it’s ugly head (slightly), Angst, Comfort, Fluff, Dean being sweet (yes, that’s a warning)

* * *

Y/N concentrated as she applied her eyeliner, her face as close to the mirror as she could get it. She had given herself a smokey eye look, with a plum lipstick to match the colour of her sequin full-sleeve, backless dress. Katie sat on Y/N’s bed of the hotel room, dressed in a black dress and heels, just watching her friend as they talked.

It was New Year’s Eve, and Katie had booked her and her boyfriend one room at a fancy hotel in the city, and another for Y/N. Katie’s boyfriend, Neil had friends who were having a big party in the penthouse and asked him to bring anyone he knew along to the party. Y/N had protested at the start, given that it wasn’t really her scene, but Katie had insisted. Somehow, they managed to find a room once Y/N had agreed.

Y/N packed up all her make-up and put it back in her make-up bag. She slipped into her black heels, fixing her hair a little as she tossed it over one shoulder and turned back to Katie.

“I mean, it’s not really our scene either, but Neil knows these guys from work. I’m sure it’ll be fun” Katie said, still trying to convince Y/N even though she was almost ready. She had just never been a fan of New Year’s. It was always a letdown.

“I know” Y/N sighed. “I’m just going to feel like a third wheel.” She hated that she couldn’t be with Dean on this night, wanting to start the new year with him. As much as she had needed to see her family and she was so glad she got to spend this time with them, she regretted not scheduling the flight back to Kansas before New Year’s.

Katie frowned, knowing what she was thinking about. “You know I’d never make you feel like that. And besides, you’ll see Dean when you get back in a few more days. So, you’ll still be starting the new year with him.”

Y/N told Katie everything when she had come over to their house before Christmas Eve, and her friend had been incredibly happy for her and the prospect of a relationship with the neighbor she had been crazy about for months.

“I guess you’re right” Y/N shrugged.

“I’m always right” Katie said, laughing. “We’re going to have a great time and bring in the new year.”

Y/N laughed at her enthusiasm, shaking her head.

Once she was ready, she grabbed her clutch purse and put her phone and lipstick inside. She opened the door and they walked out into the hallway, Y/N locking the door and placing her key card in her clutch. Katie and Neil were one floor above her, and Neil had already gone up to the penthouse, so the girls decided they would meet him up there.

Once they got inside, Y/N and Katie smiled at each other, as people danced to music, drinks were being served from the small bar set-up, and waiters walked around with them and small canapes as well. Katie spotted Neil and they walked over, and he immediately took them both to the middle of the room, where people were dancing. Y/N bopped along, but knew she needed a drink before she lost herself in the music. She got herself a gin and tonic, standing off to the side where it wasn’t too crowded. Katie gestured she’d be over in a minute, and Y/N nodded, laughing slightly.

Y/N people watched, sipping her drink. Just as she was about to move and maybe decide to join Katie and Neil rather than stand off to the side, a tall man approached her. He was wearing a fancy sweater and dress pants, his dark hair slicked back.

“Hi” he flashed her smile, but Y/N wasn’t going to do anything about it. “You all alone over here?”

“No, I’m just waiting on some friends” she replied, politely, hoping he’d move on soon.

“Okay, but are you here by yourself? Got a boyfriend?” he asked.

“I do, he’s just not here” she lied. Dean wasn’t her boyfriend, not yet at least, but she needed to get this guy far away from her.

“Well, he won’t mind if-” he started to insinuate something, and she cut him off; shut him down.

“Actually, he would” she said, glaring at him. She walked off before he could say anything, walking over to her friends.

The rest of the night went on, as Y/N ate and drank a little more, and even danced a little with Katie and Neil. Katie took a bunch of pictures, only posting the appropriate ones of her. Life of a teacher meant you couldn’t really post drinking photos, so those were avoided. She was surprised, but she had a great time, and before everyone knew it, it was twenty minutes to midnight and to the beginning of the new year. However, as much fun as she had, there was someone who she really wanted to talk to and bring the new year in with. Even if he was in Kansas, which was an hour behind New York. She explained herself to Katie, who completely understood, and they wished each other a happy new year early, before Y/N left.

* * *

As soon as she entered her hotel room, she tossed her purse on the bed and kicked off her heels. She took out her phone and tried to connect FaceTime, but the hotel’s Wi-Fi was being crappy. She dialled his number, waiting for him to pick up as she sat on the bed.

“Hey” his cheery voice came through, a little loud as she heard music in the background.

“Hey” she said, smiling. “Where are you?”

“At Sam’s. They’re having a party and invited everyone over. The girls miss you” he told her, and she guessed he found a slightly quieter room, the music now muffled in the background.

“I miss them too” she said, frowning. “And… I miss you.”

“God, you have no idea how much I wish you were here. Pretty sure I’m the only one who doesn’t have someone to kiss at midnight” he chuckled, but she frowned knowing he was definitely trying to lighten his own mood.

“Well, I left the party early. It’s nearly midnight here, and I wanted to bring it in with you” she smiled, looking out the large window of her room.

Dean smirked as he sat down on Sam and Eileen’s bed. He really missed her and was so happy when he saw her name flash up on his screen. He snuck into a quiet room so that he could hear her properly.

“What? No good-looking New York men to kiss at midnight?” he teased, but really hoping he was right.

“You know you’re the only one I want to kiss from now on” she smiled, biting her lip.

Dean licked his lips, as he smirked. “Yeah, same here, sweetheart.”

Y/N hummed, leaning back against the pillows. “Good to know.”

There was a short pause before Dean spoke next. “So… you look amazing. Your friend posted a photo on Facebook.”

“Of course she did” she laughed, slightly.

“You uh… you still dressed?” he asked, hesitantly. He didn’t know if she’d be offended by where he was going with that question.

Luckily, Y/N knew exactly where he was going with it and was very much on board. “I don’t have to be.”

She stood up from the bed and unzipped the small zip at the dip in the back of the dress. She slipped her arms out and wiggled out of the dress, dropping it to the floor. Dean smirked as he heard the rustling of fabric. Y/N picked up her phone and laid back down on the bed in just her black thong, having forgone a bra because of her backless dress.

“I wish you were here” she said, softly.

“Me too, sweetheart. You… you wanna know what I’d do if I was?” he asked, closing his eyes as he heard her whimper.

“Yeah” she said, nodding.

Dean smirked, excited about where this was going. “I’d… kiss your breasts… and lick your nipples. I’d roll them between my fingers to get them hard.”

She sighed, as she brought her free hand to her right breast, rolling the nipple between her thumb and fore-finger.

“Are you touching yourself, Y/N?” he asked, his voice husky and downright seductive.

“Yeah” she sighed, licking her lips as she closed her eyes. She could feel her arousal growing between her legs, just from her ministrations and his voice.

“Good girl” he complemented her, trying to imagine her on the bed as he talked to her. He heard her whimper when he said that and smirked as he stored it away that she was into that.

“I’d love to see you right now. See you pinching your nipples, see your hand move down your beautiful body to your pussy…” he trailed off, his own arousal building.

Y/N breathed deep, as her hand skimmed over her stomach and down to her thong, pulling it to one side. She turned her speaker phone on to free her hand, moving it to her left breast, and paying it the same attention as her right. Her fingers dipped in between her folds, feeling the wetness there.

“Dean” she moaned, softly. “I’m…”

Dean felt himself getting hard as he heard her say his name. He had longed to hear it like that for so long, and he wished he could be there to do something about it.

“You what, sweetheart? Talk to me.” His voice was low and gravelly, turning her on even more.

“I’m so wet” she gasped, as she continued to move her fingers over the folds and up and around her clit.

“Fuck” he breathed out. “Are you wet for me, Y/N? Is it all for me?”

“Yes, you. Only you, Dean” she said, smiling.

Dean groaned, palming the outside of his jeans as he felt his hard on throbbing against the fabric. He looked between the bedroom door and the master bathroom, knowing that was the only way to avoid being walked in on. He rushed over to the bathroom, closing the door and locking it. He pressed the phone between his ear and shoulder, as he undid his belt and unzipped his jeans, leaning back against the door.

“Keep touching yourself for me, gorgeous. Move those fingers inside you. Tell me how it feels” he instructed her.

She moved her fingers to her entrance, inserting one first, then another when she adjusted, pumping them in and out. She rubbed the pads of her fingers against her wall, moaning as the pleasure pulsed through her. She smiled when she heard his belt and zipper over the phone and decided to have a little fun with him in return.

“Dean, it feels so good. My fingers feel so good inside my tight, wet pussy. I… I wish they were your fingers inside me” she moaned loudly, as she writhed on the bed.

“Me too, Y/N, me too. Picture it, sweetheart. Imagine it’s my fingers fucking you, making you feel so good” he whispered, closing his eyes, imagining it himself. He pushed his boxers aside, taking hold of his aching cock, and began pumping his hand along the shaft.

“You’re touching yourself, too aren’t you, Dean?” she asked, biting her lip.

“Yeah” he groaned, as he moved his hand along his cock.

“I bet you wish it was my hand, don’t you?” she moaned, as she continued to move her fingers within her core.

“Fuck, yeah I do, sweetheart. Wish it was your fingers… wish it was your tight little pussy wrapped around my cock, squeezing around me as you take me in” he grunted, gripping himself a little tighter.

“Dean” she moaned loudly. “Oh fuck, you’d feel so good inside me, filling me up, making me feel so full.”

Dean huffed at her words. Damn she was good at this. He threw his head back, hitting the door. His jaw clenched as he moved his hand faster, chasing his release.

“Dean. Dean, fuck… oh, fuck, Dean!” she shrieked, throwing her head back as her legs shook.

“Fuck, sweetheart. You sound so fucking beautiful, fucking yourself on your fingers” he growled. “Rub your clit, baby.”

Her thumb moved over her clit, circling the bundle of nerves, causing a string of loud moans to leave her lips.

“Dean, oh my god! I-I-I I’m gonna cum… Dean, I’m gonna cum” she stammered, overwhelmed by what she was feeling.

“Do it, sweetheart. Make yourself cum on your fingers. Make yourself cum for me” he groaned.

She moved her fingers and her thumb, faster as the waves of pleasure finally crashed over her. “Ah, fuck! Dean! Dean!” she moaned loudly, not caring if people in the other rooms around her heard anything. She came hard, her fingers soaked in her release.

“Fuck… shit… Y/N.” Dean held himself tightly, pumping faster and biting back a loud groan, as spurts of cum filled the palm of his hand.

They both breathed heavily, hearing each other come down from their high over the phone. Dean smirked, chuckling to himself. This girl was really something to get him that riled up that he had to do something about it right there, in his brother’s master bathroom at a New Year’s Eve party.

He heard her breathing heavily, probably still too blissed out to talk, causing him to grin. “Y/N?”

“That… was…” she kept pausing as she tried to catch her breath. She chuckled slightly, shaking her head. She couldn’t believe she just did that with him. She had never done that before.

“That was so fucking hot” he laughed, softly.

She hummed, still running her fingers over her folds, slowly. “Yeah, it was.”

“You’re welcome” he said, a cocky grin on his face.

She laughed, shaking her head, before it slowly died down. “I’ve… I’ve never done that before. You know… over the phone.”

“Coulda fooled me, sweetheart” he smirked, as he remembered everything she said. He needed to stop thinking about it, knowing it would get him hard all over again.

“I guess when it comes to you… I just know what I want to say or hear” she shrugged, holding the phone to her ear again.

Dean smiled. “Me too.”

Before she could say something, Y/N gasped as the fireworks started. She quickly sat up and smiled brightly as she saw all the beautiful colors outside her window, high in the sky as the fireworks erupted from the bridge.

“Happy New Year, Dean” she smiled, happier than she had been in a long, long time.

Knowing that it was already time there, Dean smiled. “Happy New Year, Y/N.”

“I can’t wait to come home to you” she told him.

“I can’t wait for that either” he smirked, his heart exploding with happiness. It scared him, not knowing what could happen in the future worried him, but he had to make sure things would be okay now. He knew they would be because they were going to be in it together. They were going to be a team and work hard to make a life for themselves. Together.

“Want me to call when it’s your turn?” she asked.

“No, you just get some sleep” he replied, quietly.

“Okay” she nodded. “Goodnight, Dean.”

“Sweet dreams, Y/N” he smiled as they both hung up the phone.

Dean smirked to himself, waiting a few minutes to calm down as he cleaned up, made himself presentable again and went back out to the main room where the party was. He had done that with women before, but it was the first time in a long, long time that he had felt that satisfied without anything more. It was about them being there for each other, even if they couldn’t physically be together. That was just the beginning, and he really couldn’t wait to find out where they went from there.

* * *

Y/N’s leg bounced up and down, nervously as she waited. The waiting room was familiar, having come here every week for a year after her break-up with Ethan. Being back there brought up old feelings, but she quickly put them to bed. She wanted to go there to get her thoughts properly aligned, be sure that she was in a better headspace before she and Dean went any further than they had. She smiled to herself as thought about what happened a couple of nights ago. She had never done that with any of the other guys she had been with. She never trusted them enough to do that. With Dean, she felt like she could do anything, but she also felt like he would never judge her if she didn’t want to.

The door across from her opened, a woman walking out and down the hall, leaving the waiting room. She smiled as she saw her old therapist, Kathleen waiting with the door open. She stood up, fixed her boots over her knee and picked up her brown coat. She walked in, as Kathleen closed the door.

“Y/N” she smiled, shaking her hand. “It’s good to see you, after so long.”

“It has been a while” Y/N agreed. She knew that she could’ve seen someone in Kansas, but she knew that she needed to see Kathleen for familiarity and comfortability. She already knew her past struggles and would be able to help with her new ones based on her past experience. She didn’t want to have to repeat everything to someone new.

As they sat down across from each other, Kathleen turned to Y/N. “So… how have you been?”

Y/N looked around the office. Nothing had changed except for a few more photos of Kathleen’s kids. Kathleen was in her mid 40s now, the roots of her dark hair were beginning to grey, but she was as stylish as ever as she wore all black with chunky jewellery.

“I’ve been… good. Better than I have been in a long time” Y/N replied, with a soft smile. “I just know that I want to clear some things out of my head before I start to move on with my life.”

“Alright, so tell me what’s going on” Kathleen said, putting a glass of water in front of her.

Y/N went on to explain everything to Kathleen, stopping to clarify things when she asked. She knew about Y/N getting the job in Lawrence, that was the reason she had obviously stopped coming to see her. She told her about school, about Mark, about Lisa and of course, Dean. She told her everything, about the kiss, about giving him time with Lisa, about Mark being an asshole, about Dean being there for her when she needed him, and about their kiss before she left to come home for the holidays. She told her about the trust she had with him, but how she did fear that something would go wrong.

“I keep thinking about all the things I use to think when I was with Ethan. Like I’m not good enough, like I’ll never be able to make anyone happy. That I deserve to be alone. It all resurfaced again after Mark and now… I can’t shut it off” she explained, sadly.

“Has Dean ever made you feel that way? The way Ethan did?” Kathleen asked, her face neutral as it should be.

“No, never. Not once” Y/N said, firmly.

“He’s never said anything like that to you? Treated you that way?” Kathleen confirmed.

“No” Y/N shook her head. “He’s just… he’s so different. He’s… he’s everything I’ve ever wanted.”

“Then what scares you?” Kathleen questioned, looking at her.

Y/N huffed as thought about that question for a moment. “That… I might not be what he wants. Which is weird to even think because he’s told me that I’m it for him.”

“Have you spoken to him about this?” her therapist asked.

“No, not yet. I know I need to, though” Y/N replied, feeling tears brim against her lower lids.

“Do you think Dean would be open to having this conversation with you?” Kathleen wondered.

“I think so” Y/N nodded.

“Then, that’s your exercise. Having the conversation. Then, and only then, can you truly move forward with your life, Y/N. If Dean is the one that you want to be with, you have to make sure the past won’t creep into this relationship. You have to make sure he really knows how you feel, really knows what you’re thinking. A conversation over the phone is much different to one in person. Once he really sees you, sees how you’re feeling, that’s when you’ll know where you both stand” Kathleen explained.

Y/N sighed in relief. “You’re right. We just have to talk.”

Kathleen nodded, finally a very small smile on her face. “I’m afraid our time is up, but I’m very glad you came to see me.”

“Thank you so much, Kathleen” Y/N smiled.

“Don’t hesitate to go to someone in Kansas now. It’s difficult to repeat your past to a new person, but if you need the help… it’ll be worth it” Kathleen advised.

Y/N nodded, determined to look for someone once she got home. She might not see them straight away, but she would do her research just in case.

As Y/N left the therapist’s office and walked down the busy New York street, she smiled to herself, feeling lighter than she had in years. It was as if she had found a new voice, wanting to shout from the rooftops that she was happy. Content. She couldn’t wait to get home and see Dean. Yes, the conversation would be daunting but she was determined to do it. It would be the first step in moving forward for them, and she knew things were going to be better than ever once they spoke about this.

_This is how your story is unfolding_

_Try to grab a hold and slow it down_

_Here and now the sun is also rising_

_Day in and out, it offers no relief_

_I find my voice and sing it from the rooftops_

_Stand up tall and slowly take a bow_

_This is how_

* * *

Y/N unlocked the door of her house, sighing happily as she walked in. It was a tearful goodbye at the airport back home, with little Evie clinging to her, not wanting her aunt to leave. With a promise to be back or the promise from her sister that they would come and visit, it was set in motion that the family would see each other again, soon enough. She dropped her keys on the table by the door, unwrapping her scarf from her neck as she took off her loose-fitting grey coat. Dean had messaged her, saying he was on his way back from work while she was in the cab, and her heart was racing, knowing he’d be home any minute.

Settling her bags in the bedroom, ready to unpack later, the doorbell ringing frantically and three loud knocks alerted her. She dashed out of her room and ran down the hallway to the front door. She flung the door open, squealing as she saw his gorgeous face beaming at her. She jumped up, wrapping her arms around his neck, his automatically coming around her waist. She leaned in and kissed him, feverishly, not wanting to let go. They were locked in passion for a few moments, until the cold started to get to them. Dean walked her backwards, shutting the door behind him, blindly as he entered the house still locked in her embrace.

They slowly pulled away from each other, smiling as they took a few deep breaths.

“Hi” she sighed, smiling up at him.

“Hi” he said, smirking. “Fuck, I missed you.”

“I missed you too” she said, against his lips, kissing him again.

They continued their passionate embrace, as Y/N shuffled back towards the couch. She laid down, wrapping herself around him when he joined her. They locked lips, their hands roaming over each other, exploring each other. Her fingers scraped against his scalp as she combed her hands through his hair, his lips nipping at her neck. However, knowing there were things she needed to say to him, she gently pushed him up, smiling softly at his confused look.

“I think we should stop” she said, gently.

Not looking disappointed at all, he leaned down and pecked her lips, once. “Okay.”

He sat up on the couch and faced her, smiling softly. She smiled back at him, taking his hand in hers.

“There’s actually a few things I wanted to talk to you about” she said, trying not to show how nervous she was. “Maybe we can make dinner together tonight, then talk?”

“Yeah, of course, sweetheart” he replied, nodding. “Is… is everything okay?” His concerned expression made her smile, reassuringly.

“Yeah, everything’s good. I just need you to know some things I still have to tell you about Ethan” she replied, knowing she still hadn’t told him a few things, like she said she would when she was ready. And she was ready. “And I just think I need to air out what I’m feeling, before we continue with what we have.”

“Okay” he nodded, but still wondering what she was going to say. He wasn’t one to talk about his feelings very well, but he was going to try for Y/N. He needed her to know that this was it for him, even if he had already said it. He needed to show her now, by being there for her while she said what she needed to.

* * *

They spent the rest of the evening relaxing, watching crap TV before they started cooking. They made some fried chicken, cornbread and gravy, all of which Dean mostly did while she helped him with things in her kitchen. He insisted on doing most of it, and she was glad because even though she was a pretty decent cook herself, Dean was incredible. They talked and laughed over dinner, as they both relayed to each other their holidays and time with family, reiterating how much they missed each other.

As they moved over to the couch, Y/N with her wine and Dean with his whiskey, they sat down facing each other, the smallest of gaps between them.

“So…” she trailed off, her nerves bubbling up.

Dean took her hand, squeezing it reassuringly. “Take all the time you need, sweetheart.”

She nodded, quiet as she thought about her words. She sighed as she felt ready to talk, ready to tell him the last thing she needed to about Ethan, before she voiced her fears.

“You know most of what happened with Ethan. You know how controlling he was, how he’d tell me what I could and couldn’t do, but… you don’t know how he started telling me how I should look and dress. That dressing up meant I was trying to get attention from other men, but if I dressed down, he’d tell me I wasn’t attractive. He’d say things in the most convincing ways… and I’d believe him. I’d believe I wasn’t good enough for him… for anyone” she told him, as she avoided eye contact.

Dean looked at her as he tried to keep his anger at bay. He squeezed her hand tighter to let her know he wouldn’t let go. It was like the first time she told him about her ex. She finally looked at him, her eyes shining with unshed tears.

“It went on for a while before my family realized what was happening. They kept telling me I had to leave him, but I couldn’t see it myself, yet. I thought he was trying to make me better. I thought he loved me. We kept seeing each other, eventually moving in together. One night, we were about to head out for dinner, and he said that I should change what I was wearing. I told him it was fine, and we started arguing. He kept saying that I never listened to him, that I never did what he told me to do. I knew that wasn’t true because I always did what he asked me. Things started to get really bad and he… um…” she stopped, taking a deep breath before she continued. “He pushed me, and I fell, hit my head on the coffee table. I managed to scramble up from the floor and call the cops.”

“Fuck, Y/N” Dean whispered, shaking his head. He couldn’t believe how anyone could do that to her.

“I blacked out on the way to the hospital, so I had to stay there for a while because of a concussion. My parents helped me move things out of the apartment and move back in with them. I pressed charges and got a restraining order, but I still saw him every now and then. His family has money, so they probably bailed him out. He kept trying to apologize to me, but I was done with him. It had been a year since we broke up, but with the multiple run-ins with him before he left… I knew I had to leave. There were just too many reminders of what I had been through and I needed to go” she finished what she needed to say, taking another breath to keep from crying.

A silence fell between them, their hands still intertwined. Dean lifted hers up and brought it to his lips, kissing it softly. She smiled tentatively at him, feeling like she might explode from that gesture. He turned slightly, making sure he was really facing her properly, to look her directly in the eyes.

“I’ll never do that to you” he vowed. That statement pierced her heart as she saw a tear roll down his cheek. She knew it to be true. She knew he was the most beautiful man she could ever be lucky enough to have in her life.

“I know” she choked out, nodding to let him know she agreed as her voice gave out.

“Is that what you’re scared of?” he asked, fear making his chest tighten.

“No” she let out in a soft cry. “I’m just scared I won’t be good enough for you. That I’ll never be what you need, that this” she said, gesturing to herself and to her head, “this won’t be good enough for you. I’m a mess.”

He took the glass out of her hand and put it down on the coffee table, along with his. He cupped her face in his hands to make her look at him.

“Y/N, I need you to really hear me, okay?” he said, looking into her tear-brimmed eyes. “I want you, exactly as you are. Everything you’ve been through, it’s never gonna stop me from wanting you. You’re beautiful, smart, freaking hilarious. Fuck, sweetheart, you’re so fucking hot, you should know that from how much you turned me on that night we got each other off over the phone.”

One side of her mouth turned up in a half smile. “Really?”

“Yes” he said, without missing a beat. “Y/N… I meant it when I said this is it. You’re it for me, and I promise you that I will never make you feel like you’re anything less than the fucking goddess that you are.”

He moved forward, pressing his lips to hers, the kiss searing hot and imprinting onto her lips. She pushed herself into him, wrapping around him, never wanting to let go. She quickly pulled away, however, to look into his eyes again.

“I promise I’ll never let you go a minute without knowing how much you mean to me” she promised him.

“That’s good because… if you have worries, then I do, too” he said, shrugging.

“Tell me” she said, cupping his jaw.

“I feel like _I_ don’t deserve _you_. Like, _I’m_ not good enough for you. You’re so smart and have so much going for you… and I’m just a mechanic from a family of mechanics” he said, quietly, voicing his own fears as he looked away from her.

She shook her head, turning his head to make her look at him. “No, you’re not.”

“No?” he asked, slightly amused at how confident she was in her statement.

“No” she said, firmly. “You’re talented, and passionate and care about what you do. You’re so smart, Dean. Look at everything you’re about to accomplish with the new site. You’re amazing and I’ll never tell you you’re anything less than that.”

He smirked at her, pressing his forehead to hers. “Thank-fucking-god I helped you with your furniture.”

She laughed, as she remembered that day. The start of their story, even if they didn’t know it then. “I know.”

“So… can I take you out tomorrow night?” he asked, smirking.

“Are you asking me out, Dean Winchester?” she asked in return, playfully.

“You’re damn right I am, Y/N Y/L/N” he said, the smirk never leaving his face.

“I’d love for you to take me out” she said, kissing him, softly.

Dean slowly moved away from her, and she frowned as he walked over to the record player. He stood there for a minute, trying to decide what to play before his eyes landed on one of The Beatles albums he had. He picked it up and took it out carefully, putting it on. She smiled as he walked over to her, his hand out.

He smirked at her, offering his hand. She slipped her hand into his, loving the feel of their fingers intertwined. She pushed herself up on her toes and wrapped her arms around his neck as he wrapped his around her waist. He rested his forehead against hers, closing his eyes as she did the same.

_Something in the way she moves_

_Attracts me like no other lover_

_Something in the way she woos me_

_I don’t want to leave her now_

_You know I believe and how_

_Somewhere in her smile she knows_

_That I don’t need no other lover_

_Something in her style that shows me_

_I don’t want to leave her now_

_You know I believe and how_

Sometime after, they caught up on their favourite show for the rest of the night, slightly wrapped around each other, stealing kisses every now and then.

They both knew they would have struggles in the future, it was naïve to think they wouldn’t. They knew, however, that they could handle it because of one thing.

They were together now.

And together they could take on absolutely anything.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	12. A Lesson in Doing Things Right

**Summary for the Chapter:**

> Dean and Y/N go on their first official date. The night has to come to a close early, but not before Y/N gives Dean something to hold him over until they can be together again. A busy week keeps them separated, but a little rendezvous at the school between breaks in parent/teacher conference helps deal with not being able to see each other.

**Notes for the Chapter:**

> Warnings: Brief mentions of insecurities. Other than that, Fluff… like so much fluff. Dean being sweet AF (yes, that’s a warning). And SO MUCH SMUT. Dry humping, Semi-public, Oral Sex (Male Receiving), Vaginal Fingering, Unprotected sex (wrap it up before you tap it, people), Biting, Dirty talk, Swearing.

* * *

Before Y/N knew it, it was the next day and the day of her first date with Dean that night. Being the gentleman that he was, he left after they watched TV for a while the night before, to go sleep in his own bed. He had left regretfully, leaving her with a kiss she could still feel even as she went to bed. The sexual chemistry between them was tangible, and she wanted to almost skip the date and pull him into her bed to see what that chemistry could do. However, Dean seemed to really want to take her out and she would never refuse him.

Though it did beg the question… did they need to be going out on dates? In her heart she already knew how she felt for him. This wasn’t dating for her; this was much more. She had an inkling that he may have felt the same, considering he told her that she was it for him. Maybe some would say it was too soon to be feeling that this was what she wanted and nothing else, but she couldn’t help it. That’s how she felt. She knew he was the one since the moment they met, even if he was with someone else at the time. Everything had worked out the way it had for a reason. She was never one to believe in soulmates and people that were destined to be together, but she knew she was meant to be with Dean.

She was really looking forward to that night, but she was going to wait to bring these things up with Dean. She didn’t want to spoil his efforts to make this a special night for them. It was pretty simple, just dinner and a movie, and that’s all she needed.

Y/N was glad she had that Friday off before she went back to school on Monday and took it as an opportunity to see the girls. It was a rare occasion that Meg didn’t have a shift on a Friday, and so they took the opportunity to see each other and catch up.

They had come over and had sandwiches and soup for lunch, and they all caught up about everything they had missed in each other’s lives over the holidays. She told them about her family and how she had so much fun seeing them again, and about the present Dean had gotten her, showing them. Charlie had already seen it, obviously, but she was still happy for her friend, nonetheless.

“Please thank Dorothy as well, I know she must’ve had to pull a few strings for Dean” Y/N said, looking over at Charlie.

“It was no hassle, really. She just called in some favors that she was owed” Charlie shrugged.

There was a short pause in the conversation before Meg spoke up.

“So, Dean looked pretty happy by the time midnight rolled around for us” she started, putting her spoon down as she finished eating. “Did you have something to do with that?”

Y/N bit her lip, trying to keep the smile off her face, but failing. “Maybe.”

“I knew it. He looked way too happy when he came out of the room after talking to you” Meg grinned. “So… did you do something dirty?”

“Meg” Y/N laughed, slightly embarrassed. Charlie chuckled but made no move to stop Meg.

“Well?” Meg wondered, raising an eyebrow.

“We… may have” Y/N said, shrugging. Meg looked at her, knowingly. She knew she couldn’t keep a secret very well and they would get it out of her eventually. “Okay, fine. We had phone sex.”

Meg suddenly cheered as Charlie groaned, taking out a couple of bills from her pocket and handing them over.

“You guys bet on this?” Y/N asked, shocked.

“Meg made a bet that you and Dean had phone sex” Charlie frowned, as she watched Meg pocket the money.

“Wow” Y/N said, shaking her head. Though she wasn’t surprised by her friend doing that.

“So… how was it?” Meg asked, grinning.

“It was… intense. I’ve never done that with a guy before… but it was really hot” Y/N laughed, slightly as she described that night to her friends. “Now, I just want to be with him properly.”

“It’ll happen” Charlie said, smiling reassuringly.

“He asked me out” Y/N said, smiling. “He’s taking me to dinner and a movie tonight.”

Both Charlie and Meg looked at her, wide eyed. “Uh, excuse me… why didn’t you open with that?!” Meg asked, shaking her head.

“I meant to, sorry” Y/N chuckled softly.

“Oh my god, you’re going on your first date with Dean!” Charlie clapped her hands, giddily.

Y/N laughed at her, shaking her head. She sobered as she thought about what her friend just said. “It doesn’t feel like a first date though. I mean, we spend so much time together, we’ve been having dinner together almost every night since I ended things with Mark. It’s all felt like we’re dating… so is this really the first date?”

Charlie nodded, understanding what she meant. “Well, it’s more of an official date. You and Dean are pretty much together anyway, he clearly just wants to do it the right way.”

“I guess you’re right” Y/N nodded. “Doesn’t mean I don’t want to jump his bones.”

“Don’t worry, we’ll make you look so irresistible tonight, he can’t possibly think of anything else” Meg smiled, wagging her eyebrows.

“You don’t think it’s too soon?” Y/N asked.

“Hey, Charlie said it, you guys are pretty much a couple anyway. It’s gonna happen sooner or later” Meg shrugged, as she got up and carried her plate over to the sink.

The girls helped Y/N pick out what to wear for her date with Dean. Something that was appropriate for the type of date it was and sexy at the same time. She settled on a black dress and her black over-knee heeled boots, and her long fawn coat. As it got closer to the time for their date, Y/N got ready. She did her make-up and hair, putting a slight wave through it and settling it over one shoulder. The girls left once they gave her a look of approval and wished her luck. Y/N promised to call them and tell them how it went.

* * *

“1… 2… 3”

Dean counted down as he lifted the frame from one side, Benny on the other. They slotted the hooks on the wall into the grooves on the frame. Dean stepped down from the ladder to see if it was properly aligned and even, smirking when it looked perfect. Benny stepped down from his ladder, standing next to Dean and admiring the framed black and white photo of the Impala, that Y/N had given him for Christmas.

They had been at the new building all day along with Ellen, all three of them fixing the place up before all the new equipment and machinery came in the following week. Ellen had fixed up the reception area and some parts of the garage with Benny, while Dean fixed up the office and some of the workstations. Some of the other workers would be in over the weekend to take care of other duties as well. It had been a tiring day, but he wasn’t about to let that stop him from thinking about Y/N and their date that night.

To others, it might’ve seemed a little redundant to take her out on a date when they were practically a couple already, but it wasn’t to him. He wanted to show her what she meant to him and treat her special. He wanted to do things right this time. He had taken Lisa out on dates but there wasn’t all that much effort put into them, most of the time ending up at the diner or the bar. Things were different with Y/N. She wasn’t just any girl, she was… well, he was in love with her. He needed her to know that, even if he couldn’t say it just yet.

A bump on his shoulder alerted him that Benny was still there, a slightly amused expression on his face to see his friend spaced out for whatever reason.

“You okay there, brother?” he asked.

“Yeah” Dean nodded, picking up the ladder and walking out of the office to put it back in the corner of the garage. Benny followed behind him, doing the same.

“You spacing out wouldn’t have something to do with a little lady by the name of Y/N, would it?” Benny grinned.

Dean rolled his eyes, shaking his head. “It’s none of your damn business, Lafitte.”

Benny chuckled to himself as he followed behind Dean, back into the office. “Things getting anywhere with you two, yet?”

“Yeah” Dean said, not wanting to say too much just yet.

“You gotta give me a little more than that, chief” Benny shrugged, not budging on the topic.

“Well, considering you won’t drop it… yes. I’m taking her out tonight” Dean told him as he looked down at some papers on his desk, sorting through them.

“Nice” Benny said, clapping him on the back. “Now, why ain’t ya shouting that from the rooftops, man?” the Southerner asked, confused that Dean was being so secretive.

“Because…” Dean trailed off, as he looked at his Southern friend, dropping the papers on the desk. “I just wanna be cautious. That’s all.”

Dean didn’t want to jinx anything by making too much of it. He had gained a whole lot of luck by her coming into his life. He didn’t want to start losing it.

Benny nodded, understanding. “I get it, brother. I do.” Benny tapped him gently on the back again, a soft smile on his face. “I’m happy for ya, Dean. ‘Bout time you got a good woman.”

Dean smiled, his mind instantly on Y/N as he nodded. “Thanks, Benny.”

Dean fixed up his desk a little before he glanced up at the clock, seeing that it was time for him to leave, go home and get ready for his date with Y/N. He said a quick bye to Ellen and Benny, who were just fixing up a few things before they were due to leave as well. Dean pulled out of the parking lot to the new building, flooring his beloved Baby as he headed home.

* * *

When Y/N heard the doorbell ring a few times, she smiled as she walked out of her room and down the hallway. She opened the door and smiled even wider as she saw Dean, looking incredible in his black jacket and dark blue jeans, a black sweater underneath and a black scarf around his neck. He hadn’t shaved and she was glad for it, loving a little scruff on him. Dean looked her up and down, smirking. She looked so good as she leaned against the door, her dress and boots making her look irresistible.

“You look… you look amazing” he told her, still smirking.

“You look pretty amazing yourself, handsome” she said, leaning into him as she kissed him.

“Ready to go?” he asked before kissing her again.

She moved back and picked up her bag, smiling at him. “Ready.”

She locked up her house and followed him over to the Impala, smiling as he turned on his music and drove them into the main town square.

They got to the restaurant in time, Dean giving them his name and being led to the back where it was slightly quieter, to a table for two. They sat down across from each other and Y/N smiled as she looked around the room. It was a quaint place, exposed brick walls with black and white photos of Lawrence and of Kansas City landmarks. Each table had a candle in a glass holder, bathing the room in a warm glow. As they had walked through, they had passed the kitchen, and her mouth had watered at the aromas wafting through.

“I love this place” she said, smiling at him as they settled in.

“Yeah, it’s pretty awesome” Dean smiled, looking around. “Food’s insane, too.”

They gave the waiter their drink orders, telling him they’d need a few more minutes to decide what to eat. When he came back with their drinks, a whiskey for Dean and a glass of white wine for Y/N, they decided on what they were getting. The waiter took their orders and then they were finally alone.

“So…” she said, trailing off as she flashed him a smile.

He smirked, leaning forward and folding his arms on the table. “So…”

She couldn’t keep the smile off her face. “I’m so happy we’re doing this.”

“Me too” he nodded, as he continued to look at her. “I wouldn’t be surprised if you’re wondering why, though.”

“I kind of was.” Y/N pursed her lips, nodding. “Can I say something, and you promise not to overthink it?” she asked, hoping he’d be fine with the question she wanted to ask.

“Sure” he shrugged, not seeing a problem just yet.

“I’m so happy you asked me out on a date” she started, reaching over the table and holding his wrist. “I just think… maybe we don’t need to? I mean, I know how I feel about you. It’s way past the dating stage and it’s scary to think of that way, but it’s true-” she rambled, and Dean cut her off with a small chuckle, as he took her hand off his wrist and clasped his with hers.

“I know we don’t need to, because I… I know I feel about you, too” he said, as his thumb ran over her knuckles. “I just wanna do the right thing here, Y/N. I have to do things right this time. I took Lisa out on dates, yeah, but they weren’t much to write home about, you know? I want things to be different with you.”

She smiled, genuinely touched by what he said. “That’s very sweet.”

“Well, I’m a sweet guy, what can I say?” he grinned, his cocky attitude on full display.

She rolled her eyes as she laughed. “How humble of you.”

“And hey, what kind of a boyfriend doesn’t take his drop-dead gorgeous girlfriend out on a date? Come on” he said, feigning anger but a smile came through as he brought her hand to his lips and kissed it.

“That’s true” she said, giddy from the sweet gesture.

“And we gotta have some stories to tell our kids someday” he said, as he picked up his drink and took a sip.

She stared at him, wide-eyed. He clearly hadn’t realized what he just let slip.

“Kids, huh?” she asked, raising an eyebrow. She bit back a laugh as she saw his eyes bulge out of his sockets.

“I-I um…” he stuttered a little, as he tried to find the words to erase what he just said. When he looked at her and saw her smiling at him, with some new look in her eyes that he couldn’t quite place, he knew he didn’t need to hide away what he just said. “Yeah. Kids.”

She picked up her glass and took a sip of her wine, smiling around the edge of it. When she put it down and looked at him, she took his hand again. “Just know that I don’t need more than just you to know how you feel, but I’m glad for this date and any others all the same. And I can’t wait to tell our kids about them someday.”

If his friends could see him now, they’d rip him a new one for the full-blown chick-flick moment he was having. He didn’t care, though. He had the most amazing woman, and he was lucky to have her in his life.

He would never stop thanking whatever higher power existed for her coming here to Lawrence.

After dinner, they walked over to the cinema complex and bought tickets to an action movie. Y/N adored him for trying to say that they should go see a rom-com for her, but she told him that just because she was a girl, it didn’t mean that she liked all of the rom-coms out there. She had a feeling he was very relieved that she had insisted on the action movie. Dean bought them a large popcorn and drink combo to share, and they sat in the back row.

They munched on the popcorn as the movie played out as every other action film did. However, during one particularly steamy scene between the male and female protagonists, Y/N felt her body heating up. She crossed her legs uncomfortably, feeling hot as she sat next to Dean while the actors on screen were all over each other. She glanced over at Dean, seeing him shift slightly in his seat. Flashes of the night in her hotel room on New Year’s entered her mind, remembering how Dean had brought her so much pleasure just from his words.

At the same time, Dean was thinking about the same night, too. About how hot she sounded, about how he wanted to hear her say his name like she had that night, over and over again. You couldn’t cut the sexual tension in that cinema with a knife, as the rest of the movie carried out. They had both never been so relieved when it was finally over.

The drive back home had been silent, except for the music softly playing from the car’s radio. However, Y/N smiled to herself as she felt Dean’s hand slip into hers on the seat, in between them. He held it tightly and squeezed, lifting it as he turned his head and planted a kiss on her knuckles. When they arrived home, Dean parked the car and got out, taking her hand in his again when she got out as well. They walked across the street to her house, hand-in-hand, content to just be together. Finally.

Y/N walked up the porch stairs and to her front door, turning around and smiling up at him. She leaned up, her heeled boots giving a little more advantage to reach him better, planting a searing kiss on his perfect lips. Her arms wrapped around his neck, pulling him in deeper as his wrapped around her waist, inside her coat. She pressed back against the door as they continued their kiss, neither of them making a move to stop. Y/N pulled away and nipped along Dean’s stubbled jaw, loving the slight sting of his stubble across her lips.

“Y/N, uh, we should stop” he chuckled slightly, pulling an inch away from her to look her in the eyes.

She hummed as she combed her fingers through his hair, causing him to groan at the feel of it. “I think we should move this inside, don’t you?”

“I’d love to, sweetheart and believe me I really want to, but I gotta be up super early to uh… do something” he tried to explain as best as he could, without sounding suspicious. Which he hadn’t succeeded at because she frowned at him.

“Do something?” she asked, confused. “What?”

Dean blinked a few times, trying to think of something. He didn’t want to tell her that he had to go work on the new house, considering he completely envisioned her in that place. He wanted it to be a surprise for their future together.

“I can’t say, not yet at least” he replied, looking sheepish.

She raised an eyebrow as she looked at him but decided not to push any further. She trusted him and she knew that he’d tell her when he was ready.

“Okay” she nodded, slightly disappointed.

“I’m sorry, sweetheart” he whispered as he leaned in and kissed her nose.

“It’s fine” she shrugged, trying not to let it get to her. She turned around and faced the door and was about to put the key in the lock when Dean wrapped his arms around her waist, locking her in his embrace. He nuzzled his nose along her jaw, and kissed her cheek, softly.

“I’ll make it up to you, soon. I promise” he smirked, tilting his head to look at her.

Feeling him extremely close to her, his front to her back, gave her a naughty idea which she couldn’t get out of her head now that it was in there.

“I know” she said, turning her head to look at him. “But in the meantime, maybe I can leave you with a little something…”

She emphasized her words with a small tilt of her hips, pushing them back into his. He hummed as he felt her ass against the crotch of his jeans, his cock twitching slightly in his pants.

“Don’t play dirty with me, sweetheart” he growled in her ear. A shiver ran down her as she bit her lip, rubbing into him again. She could feel herself getting wet between her legs.

“Somehow I think you like that” she sighed, as she leaned back and pecked his lips. She took his hands in hers, moving them to hold onto her hips. She slowly began rutting back against him, his groans alerting her to his arousal. She moaned as she felt his cock becoming hard, straining against his jeans.

“Shit, Y/N” he hissed, feeling the pressure in his pants and not being able to do anything about it. He glanced around, hoping that no one would come out of their houses and see them. “Someone could see us.”

She shook her head, not letting him move away. “It’s okay, baby. It’s a quiet street, no one’s going to know.”

Dean thrust his hips forward against hers, growling as he felt his cock press against her ass every time he moved forward. She took his hands and moved them up her body, moving her coat back as she planted them on her breasts. He grunted as she pushed into him a little harder as their hips continued to meet, his covered hard on rubbing against the fabric of her dress over her behind. He could feel that he was about to lose it, as they continued to grind against each other.

“Fuck” he bit out through clenched teeth. He palmed her covered breasts, leaning in to kiss her neck. “Shit, sweetheart, fuck” he huffed as he groaned.

“Dean” she moaned, as she glanced back at him. Seeing her hooded eyes as her perfect mouth hung open from the pleasure that coursed through her, pushed him over the edge.

“Fuck, Y/N” he grunted as he leaned his forehead on her shoulder, shaking as his seed released inside his jeans.

Y/N smiled as she felt him breathing heavily, his chest against her back. She didn’t cum, but that didn’t bother her when it came to Dean. This was about him and just giving him another little preview of things to come for them.

“I feel like a teenage boy.” He shifted uncomfortably, his jeans no doubt stained now.

“You’re fucking full of surprises, sweetheart” he chuckled, as he nuzzled into her neck.

She laughed a little as she turned around, cupping his face in her hands. “You have no idea.”

She leaned in and kissed his lips, smiling into the kiss. He pulled away and looked at her, lifting a hand to stroke her Y/H/C hair back as he cupped her face.

“I better go” he whispered as he looked into her Y/E/C eyes. He leaned in, softly kissing her lips. “I’ll call you tomorrow after I’m done.”

“Okay” she said, smiling at him.

Dean stepped back from Y/N, winking at her before he turned around and walked down the porch stairs. Y/N went into her house, locked the door and practically screamed as she thought about everything that had just happened outside, a few minutes ago. She couldn’t believe she did something like that but as she had already realized, when it came to Dean, she lost all her inhibitions.

As she got ready for bed, she couldn’t stop thinking about how things were already so amazing between the two of them, and they were only going to get better.

Dean cleaned himself up and got dressed into a black shirt and sweats. When he climbed into bed and stared up at the ceiling, he smirked as he thought about Y/N. She kept surprising him, and he loved that. Given their age difference he had to keep up with her a little, but she was incredible in every way.

She was going to be the death of him, he was sure of it, but damn it if she wasn’t the most amazing woman he had ever been with.

* * *

The next few days were incredibly busy for both Y/N and Dean. He was busy with everything at the new garage, and she was busy with getting back to school and the start of the next semester. They had parent/teacher conference as well, so that added another layer of stress to that week.

The day of the parent/teacher conference was a long day. A day of classes first, and then once the kids left, the teachers set up their classrooms and made them look fancy with all the projects. Y/N had set up the room with different quotes from books and photos of literary figures, some that they had already studied and some that they would in the future. Parents of every form were there; couples still together, couples divorced and co-parenting, single moms, single dads and foster parents.

She was happy that she had this opportunity to meet them, and she was glad that things had become better, with almost all of the kids doing well. Some were at higher levels than others, but everyone was doing as well as they could in terms of their aptitude, and Y/N felt good about that. There were a couple, however, that she knew were going to have trouble in high school if they didn’t turn it around, quickly.

In between sessions, Y/N scrolled through her phone’s social media apps, texted Charlie and Cas down the hallway if they could take a break at the same time as her. After about only 15 minutes of catching up, however, they all had to go back to their next meetings. The hours were ticking by slowly, as she kept herself entertained with a book in between meetings. At another break, she was trying to read but she just couldn’t concentrate. Looking at the time, she realized that it was 6.30pm. Dean would’ve finished work half an hour ago, so she decided to text him.

**Y/N:** _Currently waiting on my next meeting, but I’m so bored. I keep trying to read but I think I’ve read the same line 500 times in the last few minutes._

**Dean:** _Well, I literally just finished work and on my way home!_

**Y/N:** _Oh no! What happened?_

**Dean:** _Eh, late deliveries that I had to wait around for. Dinner might be late, unless… pizza tonight?_

Y/N bit her lip as an idea came to her. Now that he wasn’t making dinner and they could always order pizza a little later, she wanted to see what he thought about her idea.

**Y/N:** _Sounds good, but maybe we can hold off on it for a bit?_

**Dean:** _Uh… I guess. Why?_

**Y/N:** _Do you think you can come to the school?_

**Dean:** _What are you up to, sweetheart?_

**Y/N:** _Why don’t you come here and find out? ;)_

Dean stared down at his phone, every possibility of what she wanted going through his head. He shook his head. It couldn’t be what he was thinking.

**Dean:** _Do I want to?_

Y/N smiled as she shook her head. He clearly didn’t realize she was being serious about him coming to the school.

**Y/N:** _Yes ;)_

Dean choked at that message. Was his teacher fantasy about to play out? He almost couldn’t believe it.

**Dean:** _On my way!_

Y/N laughed at the gif of a car speeding that he had added.

**Y/N:** _Give me 15 minutes with the next parents, and then I’m all yours, handsome_. She added a heart emoji.

Dean couldn’t help but let out a groan when he read that.

**Dean:** _Damn right you are ;)_

Y/N felt a shiver run down her body as she bit her lip, reading his message. She had no idea what was going to happen once he got to the school, but damn she was excited to find out. The haze of arousal was broken however, when the next parents came in. They were talkers and the meeting went a little over time, but eventually they were both satisfied with everything Y/N told them. They thanked her and left, leaving her to wonder when Dean was going to get there. She stood up, took off her glasses and shut the lid of her laptop and was just about to message Dean and see where he was, when a light knock on the door interrupted her.

She smiled when she looked up and saw Dean leaning against the doorframe, smirking at her. He walked in and closed the door behind him, locking it, and pulling the blind down over the window in the door.

“I came in when the parents were leaving” he said, as he walked over to her. He gently pulled her towards him by her hand, her body close to his as he wrapped his arms around her waist. She smiled up at him, her arms automatically wrapping around his neck.

“I’m glad you did, but there’s still some people here so we have to be quiet” she told him. Even with her heeled knee-high boots on, she still had to push herself up slightly on the toes, to press her lips to Dean’s. “And… we have to be quick before the next meeting in 20 minutes.”

“Oh really?” he grinned. “What’re you planning on doing to me in 20 minutes?”

She hummed against his lips, her fingers combing through the short hair at the back of his head. “So many things. I’ve barely seen you; you’ve been so busy with the new site and I’ve been busy with everything leading up to tonight.”

He groaned, as one of his hands slipped down slightly, laying over one side of her behind, covered by her grey A-line skirt. “Fuck. I know. I swear, when things calm down slightly and it’s just up to the contractors to get all the heavy machinery into the site in the next few days, I’m taking you out.”

“I look forward to that, but I hope that doesn’t mean we can’t do a few things right now” she whispered against his lips.

“Definitely not” he whispered back, finally claiming her lips in a searing kiss.

If it were even possible, they pulled each other in even tighter, their bodies moulded together as they continued to kiss, passionately. Y/N softly bit Dean’s bottom lip, causing him to open his mouth and deepen the kiss. She moaned into the kiss, feeling his hand press a little harder into her ass. She pushed into his body, causing him to take a few steps back until his back was pressed against the wall. Her arms came away from his neck, her hands roaming over his muscles through his jacket and moving down his chest.

Her hands moved under his maroon button-up and pushed it off along with his jacket, Dean taking over in removing them completely and tossing them on the floor. Her lips moved away from his, kissing and nipping along his jaw, moving down to his neck. He groaned as she nipped at his neck, his hands groping her ass. Her hands moved over the black t-shirt covering his chest, and down to the outside of his jeans, feeling that he was getting hard already. She rubbed her hand along the seam of his jeans, feeling him grow harder. Dean hissed, feeling the pressure of his cock against the fabric of jeans. Suddenly, Dean stopped for a second, looking around. “Are you sure about this?”

“Of course,” she said, as she cupped his face. “Dean, what’s wrong?”

He smiled at her, a little sadly. “Should our first time really be like this?”

She smiled at him, her heart bursting with love at his concern. “Dean… I want you. I know you want me, too. I know you keep saying that we should do things right, but what’s right is you and me. Does this feel wrong to you?”

“No” he said, shaking his head, his response quick and firm.

“Then… there’s no problem, right?” she asked, biting her lip.

He groaned as he looked at her doing that. That always made him weak. “Right.”

Y/N smiled at him and went back to what she was doing. She unbuckled his belt and pulled it through the loops, tossing it behind her. She unbuttoned and unzipped his jeans, pushing them down slightly. She pulled down his boxers and gasped as his cock was on full display, hard, as his length and girth made her mouth begin to water. He was bigger than any of the other men she had been with, and she felt her heart begin to beat faster. She lightly grasped it, her hand moving slowly along the shaft. She stared into Dean’s eyes and smiled, biting her lip. He let out a shaky breath as he looked at her, his eyes clouded with arousal. Her fingers moved over the tip, feeling pre-cum drip out onto her fingers. She took his cock in both of her hands, pumping them up and down as she moved down to her knees.

Dean groaned as he watched Y/N get on her knees, his cock in her hands. She leaned forward and kissed the tip, her tongue circling the head. She sucked at the head, slowly taking in more of him, inch by inch. Her hand grasped the base of his cock, pumping up and down as she bobbed her head, wetting the shaft with her saliva. She looked up at him as her other hand cupped his balls, massaging them in her hand.

Dean grunted, throwing his head back against the wall, his mouth hanging open. “Fuck, sweetheart. You’re so fucking good at that.” He looked down at her, his thumb stroking her jaw, as her cheeks hollowed while she continued to take him into her mouth. “Love seeing your mouth on my cock.”

She moaned loudly as she drew back and pulled her mouth off him, her hand continuing to move along his dick. “Your cock feels so good in my mouth, Dean. I can’t wait to feel you inside me.”

Dean couldn’t wait for that either. He took her hand off him and tugged, making her stand up. Her mouth felt incredible, but he definitely didn’t want to cum yet.

Y/N let go of Dean’s hand and moved hers under the waistband of her skirt, pulling out the end of her black, full sleeve top. Dean moved her hands away, taking over as he pulled the end of her shirt over her breasts, revealing her dark red bra. He reached up and pulled the cups down, her nipples pebbled and aching against the slight chill in the room. He leaned into her right breast, kissing her flesh, his tongue circling the nub. She grasped his hair in her hands, bringing him in closer.

“Dean” she gasped, as he sucked and nipped at her, moving to her left and doing the same.

Dean bent his knees, grasping the bottom of her skirt and bunching it, revealing her matching panties. His hand moved in, his fingers rubbing along the outside of the fabric, feeling how wet she already was.

“Shit, you’re so wet sweetheart. Did sucking my cock turn you on that much?” he asked, his voice husky as his fingers moved faster along the fabric.

She let out a shaky breath, as she nodded. “Yeah.”

“Yeah?” he chuckled, slightly.

She nodded, frantically as his hand continued to move. “Dean…”

“What, sweetheart?” he asked, kissing her nipple.

He hooked a finger in her panties and moved them to the side, groaning as he felt her wetness against his fingers. He ran them along her folds, his thumb flicking lightly over her clit.

She moaned, her chest heaving as she breathed deeply. “F-fuck me. Please. Please fuck me.”

Dean moved them backwards, until her ass rested against the edge of her desk. He grasped her thighs and lifted her up, sitting her on top of it.

Dean’s hands moved down along her thigh-high stockings, biting his lip as he felt her soft flesh against his fingers. She wrapped her arms around his neck, pulling him for a heated kiss. Her hand cupped his jaw, bringing his mouth tight against hers. They parted when they needed to breath, as she wrapped her boot-covered legs around his hips. Dean lifted his black shirt up and took it off, her hands immediately roaming over his muscular arms and shoulders, his hard but soft torso. She bit her lip, keeping herself from moaning too loudly at the sight of him. He was truly the most gorgeous man she had ever been with. Dean moved closer, as he took hold of his cock, pumping his hand along the shaft a few times.

He stopped, however, when he realized something. “Shit, I don’t have any-” he started but she cut him off with a quick kiss to his lips.

“I’m on the pill” she nodded as she looked into his eyes. “We’re good.”

He smirked slightly, as he looked at her. “Okay.”

He took hold of cock and guided it to her entrance, pressing the tip in. He moved forward, slowly sinking into her warm cavern. She hummed at the feel of him, her walls stretching to accommodate his size. He gave her a second to adjust, before he slowly started to pull out. He pushed back in, setting a slow rhythm.

“Y/N” he moaned, softly. “Fuck, you’re so fucking tight. So fucking perfect.”

His hips met hers, as he gradually picked up the pace. He thrusted into her at a moderate pace, causing her to moan loudly, forgetting where they were.

He laughed as he pressed his lips to hers. “Shh, sweetheart. Can’t let anyone hear us.”

She whimpered, as she moved her hips against his. “Fuck, Dean.”

Dean growled low, feeling it rumble in his chest. “Shit, sweetheart. You feel fucking amazing wrapped around my cock.”

“Dean” she moaned quietly. “Fuck me harder.”

“Harder, huh?” he grinned, pressing his forehead against hers. “Like this?”

He drove his hips in, the drag of his hips longer as he continued at the pace he had set, but his cock moving in harder and deeper within her.

“Yes” she gasped. “Just like that. Oh god, Dean.”

“You like that?” he asked, as he looked down at his cock driving into her.

“Yes” she moaned, her voice choked as she tried to stop herself from raising her voice.

She threw her head back, exposing her neck, her chest pushing out. Dean leaned in, kissing her neck, along her collarbone and down the valley of her breasts, feverishly. She moved in, wrapping her arms around him, tightly. Their faces were close to each other, their hot breath mingling as they let out small moans, gasps and groans. Y/N leaned down, sinking her teeth into Dean’s shoulder as she tried to stop herself from moaning loudly. Dean hissed at the sting of her teeth on his flesh but moaned softly as it added another layer of pleasure to what he was already feeling.

Dean’s hips picked up pace, the desk underneath them beginning to rock back and forth from the force of his thrusts. Y/N pressed her lips together, trying to keep quiet, as her hips met his, matching his pace. They were both close.

“Fuck, Y/N” he grunted, pressing his forehead against hers.

“Dean” she moaned, opening her eyes and staring at him. “I’m so close.”

The coil began to wind up tight in her core, ready to break at any moment. She whimpered as he grabbed her hips and drew her in closer, his cock hitting her g-spot with every thrust.

“Cum for me, Y/N. Cum on my cock” he groaned, his hips unrelenting.

Items on the desk began to shake, and Y/N knew she had to get to her release before something fell and alerted someone to what was happening. Somehow Dean understood when she looked down at the lamp shaking; he quickly licked his fingers and brought them to her clit, circling the little bundle of nerves in tight, fast circles.

She let out a harsh gasp, her mouth hanging open as the coil snapped, panting quick, shallow breaths as she came. Her release slicked his cock, warm and wet against him. Dean’s thrusts became erratic, stuttering as he approached the edge.

“Dean” she moaned as she cupped his face, looking into his eyes. “Cum inside me.”

He panted, his breath hot against her lips, letting out a choked grunt as he thrust into her few more times, falling over the edge as he came inside her. He leaned his head on her shoulder, his hips slowing into shallow thrusts. He slowly pulled out of her, as she felt his seed drip out of her.

Y/N leaned her cheek against his head, combing her hand through his sweat soaked hair as they both came down from their high, breathing deeply. After a few moments, he slowly lifted his head, looking into her eyes. She smiled at him as he smirked, both of them laughing quietly. He leaned in, kissing her softly, a change of pace to how he had just fucked her, showing that he was as sweet as he was incredibly sexy. He kissed her lips, once, twice, three times before slowly moving away from her.

Y/N reached over and took out some tissues, cleaning herself as she passed Dean a few as well. He cleaned up and then pulled up his boxers and jeans, buttoning them up and pulling up the zip. He picked up his belt from the floor and put it through the loops, buckling it. She fixed her panties and pulled her skirt down, fixing the cups of her bra and pulling her top down, tucking it back in. Once they had redressed, Dean walked over to her as he shrugged on his jacket. He held her hips as he leaned in, kissing her again.

“You should head home” she told him, smiling. “I’ll be there in another hour.”

“Okay, I’ll order the pizza” he said, cupping her cheeks in his hands. “Should be there by the time you get home.”

“Sounds good” she said, still smiling.

There was a moment of silence between them as they looked at each other.

“That was amazing” she said, feeling her cheeks heat up.

“Fuck yeah, it was” he grinned, his eyes lighting up.

She laughed at him as she lightly smacked his chest.

“I’ll see ya in a bit” he whispered against her lips, kissing her softly.

“Yeah” she whispered as he pulled away.

Dean walked over to the door and unlocked it. He opened it and turned back to her, seeing her watching him. She looked even more beautiful with her lips slightly swollen from kissing, and the knowledge that he had just ravaged her almost got him hard all over again. With one last look and a wink at her that caused the most beautiful smile to grace her face, he left and walked down the hall, ready to head home and wait for her.

Y/N fixed everything on the desk which had moved during their rendezvous. After the last few couples came in for their meetings, she packed up her things, put on her coat and scarf and shut off the light in the room. She walked down the hallway, the heels of her boots echoing off the floors.

As she drove home, the smile just wouldn’t leave her face. What they did back there, had been everything she could possibly want. It had been everything that they both needed. It solidified everything they both wanted from each other and for their future.

They were each other’s future.

And that was the biggest reason to smile.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	13. A Lesson in Meeting Family (Part 1)

**Summary for the Chapter:**

> A busy few days keeps Dean and Y/N from having any fun together, but a Friday night makes up for that. Later, Dean and Sam talk about his relationship with Y/N, prompting Sam to tell Dean to bring her over for dinner. Nervous and hoping she doesn’t mess up, Y/N realizes how much she truly wants to be a part of the Winchester family.

**Notes for the Chapter:**

> Warnings: Minor angst, Dean being a mystery man, Nerves, Anxiety, So much fluff, A WHOLE LOTTA SMUT. Oral Sex (Female receiving), Swearing, Dirty talk, Biting, Unprotected sex (wrap it up before you tap it, people!)

* * *

The rest of the week had remained busy for both Y/N and Dean. He had to oversee everything new that was coming in at the new garage, wanting everything to look perfect and up to his standards, while Y/N had a few extra parent meetings during the rest of the week with those who couldn’t make it to the conference night. By the time they came home, they were both so tired that they could barely have some fun with each other. That being said, falling asleep in each other’s arms had been the best thing to end their busy days, and they were both glad they could do that.

When Friday eventually rolled around, they had both never been happier about it. Y/N was bouncing on her heels all day at school, anxious to get home and be with her boyfriend. She had gotten a couple of weird looks from the kids, an “are you okay? You’ve been acting strange all day” from Charlie, and Cas’s classic puzzled face as he tried to figure out what was going on. It was funny, but if she hadn’t been so fired up and horny all day, she would’ve found it even more amusing.

As soon as the bell rang to signal the end of the day, the kids packed up their things and filed out of the room. Y/N made sure they all got out and either got to the people who were picking them up, on the bus or on their bikes, before she packed up her own things and headed home. She had a good 2 hours before Dean would be home which meant she had plenty of time to cook her fettucine alfredo he loved so much, and also get ready for what would happen for the rest of the night.

When she got home, she made quick work of making dinner. It had all taken her an hour, which gave her another hour to get ready. He had no idea that she was doing all of this and she couldn’t wait to see the look on his face when he got home.

She had a quick shower to freshen up, and then got changed into a black bra with lace detail that came to just above her belly button, black silk shorts with lace detailing on the edges, and a light grey silk robe, with black lace detailing on the ends of the sleeves and edges. She fluffed her Y/H/C hair a little to open it out, applying a little make-up to add to the sultry look.

She smiled as she admired herself in the mirror. Dean didn’t know what was about to hit him.

* * *

Dean was hunched over his desk in his office, filling out orders for parts that they needed for some of the cars. He was at the old site that day, as he and Benny were taking turns of who was going to look after the new one each day. Once things were more settled, they would handle it on a week-to-week basis, and then eventually trust some of the other guys that worked for him and bring them into the schedule as well.

Luckily, today had been a light day in terms of work and it was mostly just boring paperwork and orders that needed to be filled. It meant he wouldn’t be tired by the time he got home. His mind had been on Y/N all day, thinking about all the things he was going to do with her once he finally made it home. After that night in her classroom, he couldn’t wait to see how much better things would be once they were in their own space. Absolutely anything was possible, and he had to keep calming himself down all day as he thought about the possibilities.

He finally clocked off at 6pm, locking up the office and leaving the last worker to close up once he was done with the car he was working on. He drove home, the drive shorter from the old site than the new one, which was a few minutes outside of the main area of Lawrence. He parked Baby at the house, and rushed over to Y/N’s, escaping the bitter chill of January as quickly as he could. He knew that she would’ve left the door unlocked to him closer to 6pm, and sure enough, he walked in and locked the door behind him.

“Hey, sweetheart!” he called out, and shrugged off his jacket. He hung it up on the hooks by the door and took off his scarf, hanging that up as well.

He heard AC/DC playing, smirking as _You Shook Me All Night Long_ greeted him as he stepped through the threshold.

Having heard the door open, Y/N sat on one of the high stools at the kitchen bench, crossing her freshly shaved legs and leaning back in the chair, her hand in her hair. Dean walked down the hall, his boots echoing on the floor, which stopped short once he came into view. His eyes widened as he saw her and that gorgeous smile of hers. His eyes travelled to every expanse of exposed skin, and he could already feel himself getting hot under the collar.

“Hey, baby” she said, her voice sweet yet incredibly sexy at the same time.

“What is all this?” he asked, looking around the room. There were two place settings at the table, candles lit and a bottle of white wine on the table. He could smell the beautiful aromas from the kitchen; smiling when he realized it was the smell of her fettucine, he was absolutely crazy about.

“I just wanted to do something special for you” she smiled. “For us, considering we’ve barely had any time together this week apart from at school.” She wagged her eyebrows, biting her lip.

“You’re amazing” he smirked, as he started walking closer to her.

“I hope you’re hungry” she said, looking over at the large pot resting on the stove.

“Oh, I am” he nodded, as he took short strides towards her, building up the anticipation of the moment. “But the pasta can wait.”

“Oh really?” she asked, lifting an eyebrow.

“Really.” He reached her, his arms automatically wrapping around her waist and pulling her flush against his body. “There’s something else I want right now.”

He lifted her off the stool, causing her squeal as he held her close, her feet dangling above the ground. He leaned in, kissing her passionately, their lips moulded together perfectly. She wrapped her arms around his neck, her fingers combing through his hair. Dean moved away from the kitchen bench, walking blindly down the hallway to her bedroom, but making it there without any worries. He gently laid her down on the bed, standing at the edge and admiring her.

_She was a fast machine, she kept her motor clean_

_She was the best damn woman that I ever seen_

_She had the sightless eyes, telling me no lies_

_Knocking me out with those American thighs_

“God, you are so fucking beautiful, Y/N” he said, lifting her left leg up and kissing her ankle.

She smiled up at him and let out a small gasp, as her continued a path up her calf, her knee and her thigh with his lips. He leaned down on top of her, kissing her as his hand rubbed her mound over her silk shorts. He laid a trail of kisses and small playful bites along her jaw, her neck, between her breasts encased in lacy material, as he travelled down and licked a small path along her stomach, softly nipping at her belly button. She laughed a little as she squirmed, meeting his eyes as his face hovered close to her mound.

Dean slipped his hands into the waistband and slowly pulled her silk and lace shorts down her smooth legs. He spread her legs more to give him access as he laid down on his stomach, his eye contact never breaking hers. He was still yet to do this, and that was completely shocking to him considering it was his favorite way to please a woman. Watching them come undone all because of his tongue… there was no better thing to witness, and now he only wanted to see Y/N in the throes of bliss. All because of him.

Dean leaned in, slowly letting his tongue lave over her folds, feeling how wet she already was. She gasped as she closed her eyes, bringing her bottom lip between her teeth. His hands curled around her thighs as he continued his slow ministrations, gaging what she liked. He moved in a little more, his tongue licking along the wet, hot cavern, causing her to moan loudly. He smirked as he moved up, his tongue circling the sensitive bud, making her throw her head back.

“Dean, shit” she moaned loudly as she opened her eyes and looked down at him. “Just like that.”

“You like that, sweetheart?” he murmured against her skin.

“I love it” she whimpered.

Dean moved his tongue in tight, slow circles around her clit, groaning as he felt her hands grip the short spikes of his hair.

“You taste so fucking good, Y/N” he muttered, as he sucked at her folds. “So wet, so perfect… just for me.”

Dean drove his tongue into her entrance, as he slowly began to move in and out, feeling the ridges of her walls against his tongue. He smiled as he looked up at her, seeing her back arch off the bed, her hands gripping his hair tighter. She looked so damn beautiful as she experienced what he was doing to her.

“Fuck, oh my god, Dean” she was panting heavily, the pitch of her voice growing as he continued to please her. “Fuck! Dean! Your tongue feels so fucking good, don’t stop.”

He continued to thrust his tongue into her, driving deeper, feeling her get wetter as he continued. He moaned against her as he tasted her, the vibrations moving through her whole body. He moved his tongue back to her clit, circling it faster than before. His right hand moved away from her thigh, coming up to her entrance. He inserted two fingers, thrusting them in and out, at the same pace that his tongue had previously kept. Between the squelching sounds of her wet canal and his moans or groans of enjoyment from the pleasure he was bringing her, everything she felt in that moment was completely overpowering.

She cried out, too overwhelmed at all the sensations she was feeling. “Dean, fuck… that feels so fucking good!”

He sucked at her clit, thrusting his fingers faster. He released the bud from his mouth with a pop, kissing her thigh. “Your pussy tastes so fucking good, sweetheart… can’t wait for you to cum on my tongue.”

“Fuck” she gasped, carding her fingers through his hair, driving her hips forward onto his fingers.

“You’re close, aren’t you, Y/N?” he asked, his fingers continuing to thrust into her.

“Yes! Yes… I’m so close” she replied, her breath pitchy, as it remained high.

“Cum on my tongue, gorgeous… let me taste you” he growled. He moved his fingers to her clit and his tongue back to her entrance. He rubbed her swollen nub in tight circles, as he drove his tongue in. He continued his ministrations for just a few more seconds before her hands clenched his hair even tighter.

“Oh my god, Dean! Yes… yes! Dean!” she yelled, her whole body quivering as the damn broke, and she came harder than she ever had, on his tongue.

Dean lapped at her folds, moaning against her as he tasted her. He felt her fingers unclench in his hair, as her body relaxed. He looked up at her and watched her chest heaving as she came down from her climax.

Satisfied with having taken everything she gave, Dean leaned up and looked down at her. She opened her eyes as she continued to breathe heavily, smiling up at him. He leaned down and kissed her, smirking when she pulled him in closer. She moaned at the taste of herself on his mouth. No other man had ever done that as well as Dean had.

He pulled away, still smirking. “You okay?” he asked, combing her hair as he cupped her cheek.

“That was fucking amazing” she replied, shaking her head with a laugh.

“Glad I could be of service” he grinned, dodging her hand when she playfully tried to smack him.

“No one’s… well, no one’s been able to do that for me quite as well as you” she told him, as she smiled.

Dean smirked, a sense of pride washing over him. “Well… I’m happy I’m the only one who gets to do it from now on” he said, wagging his eyebrows.

She sat up and quickly removed her robe and bra, her hands immediately going for his layers. She grabbed his flannel and yanked it down his arms as he tossed it away, going for his black shirt and pulling it up, not caring where it fell as he threw that on the floor too. She undid his belt, zip and button to his jeans, watching him kick off his boots and socks before pulling his jeans down. She admired his cock, a naughty smirk gracing her face as she saw how hard he was.

“I need you to fuck me hard” she said, looking up at him as she laid back. She grabbed his shoulders and pulled him down on top of her. He was almost flush against her body, holding himself up just a little by his forearms. She planted her feet on the bed with her legs spread, letting him get closer to her.

“Oh, I will, baby” he said, kissing her hard on the lips. “I’m gonna fuck you so hard you’ll scream my name loud enough for the whole damn street to hear.”

Knowing she was already more than ready for him, Dean held his cock to her entrance and thrust into her, sliding all the way into her that it felt like he was hitting her cervix. He slid back a little before moving back in, his hips immediately picking up speed.

“Yes, oh fuck” she sighed, as her hands moved down his sculpted back and rested on the globes of his ass. Her hips met his, matching his pace.

“Fuck, you feel so damn amazing, Y/N” he groaned, his jaw clenched. “So fucking perfect around my cock… could fuck you all night.”

She moaned, her fingers digging in the flesh of his perky behind. “I hope you do.”

“Shit, Y/N” he huffed as he leaned down, kissing her as hard as he moved into her.

She moaned into his mouth, their breath mingling. “Your big, hard cock feels so good inside me, Dean. You fuck me so good, so deep…”

He grunted as he leaned down and sucked at her pulse point, biting her slightly which caused her to let out a loud gasp. One hand left his ass and combed into his hair, yanking it back. He growled as he looked down at her, her eyes dark with pleasure and mischief. He leaned up and stayed on his knees, planting his hands on her hips. If it were possible, his hips drove into her harder, his thrusts relentless as he pulled her onto his cock, his hips hitting the back of her thighs, as his balls smacked against the curve of her ass.

“Oh, fuck! DEAN!” she screamed, her back arched as she gripped her hands into the sheets underneath her.

He looked down at where his cock drove into her, feeling her clenching around him with each thrust. “Look at that… fucking taking my cock so good, sweetheart.”

She palmed her breasts, causing him to grunt as his eyes raked over her body, glistening with sweat.

“Dean… fuck… I’m-I’m gonna cum again” she whimpered, groping her breasts. She pinched and flicked her nipples between her thumb and forefingers to build her climax.

Dean leaned back down into his previous position, causing her arms to wrap around him and bring him closer. Their bodies were moulded together as they held each other tight, their hips slowing down into a sensual pace, but still hard.

“Cum with me, Y/N” he said, as he gazed into her eyes.

Their hips met in a few more thrusts, before she moaned his name, over and over again, as the waves of pleasure pushed her over the edge. Dean let out a strangled grunt when her walls clenched around him. His cock pulsed inside her, spurts of his release flooded her entrance, filling her up.

They breathed heavily, neither of them wanting to let go of each other. Eventually, Dean felt too stiff and slowly removed himself from her, watching his cum drip out of her entrance. He rolled onto his back onto the bed, his hand combing through his sweat soaked hair. He smirked as he felt her hand on his sweaty chest, kissing her wet forehead as she leaned her head on his shoulder. He looked into her eyes, the smile never leaving his face.

“We…” she started, taking deep breaths to return to normal. “We’re never going… more than a day without doing that.”

Dean chuckled, nodding. “Yeah… three days… not doing that again.”

She smiled, as she lifted her leg and wrapped it around his hips, her hand coming up to trace lazy patterns on his chest. “Never.”

“Hey, didn’t you make dinner?” he laughed, his mind hazy after that incredible experience. She was truly something else. He would never stop feeling lucky to have her.

She laughed along with him, nodding against his shoulder. “We better eat.”

“Yeah” he said, as he grinned down at her. His eyes sparkled with a mischievous look. “Gonna need all the energy I can get for round two.”

She leaned in and kissed him, once, twice before they sat up and cleaned themselves off. He put on his shirt and jeans as she wrapped the robe around herself, tying it at the front. They went into the kitchen to eat the meal she had made for them, now completely ravenous.

They spent the rest of the night talking, laughing, kissing and getting in round two and three before they settled under the covers, falling asleep peacefully in each other’s arms.

* * *

“Four times?!”

Y/N shushed Meg as she exclaimed loudly in the bar, people around them glaring at them. Charlie waved them off with apologies, before turning back to the conversation.

Saturday night saw the friends out for drinks after a simple dinner. Charlie and Dorothy sat on one side of the table, Meg and Y/N on the other. Meg wanted to know all the details of her date with Dean, which she did tell them, followed by what happened at the school and then what happened the night before. She made the mistake of telling Meg how many times they had done the deed, and now people were giving them the stink eye.

“He made you cum four fucking times?” Meg asked, her voice lower this time.

“Yes” Y/N replied, her face heating up and not from the Negroni she was drinking.

“Holy shit” Meg gasped, her eyes wide. “Fuck, I’m so happy for you. You totally deserve this after that asshole who couldn’t even get you to cum once.”

Y/N laughed at her weird show of happiness. “Thanks for caring about my orgasms so much.”

Charlie snickered into her drink, as Dorothy rolled her eyes playfully at her girlfriend.

“I mean it, seriously” Meg said, taking her hand. “Good for you.”

Y/N nodded, genuinely agreeing. “It is good for me. Fuck, it’s the best sex I’ve ever had.”

Meg laughed, clapping her hands. “Oh my god. This is amazing… finally proper confirmation on Dean Winchester being a sex god.”

“Yeah, we’ve heard the stories from the guys, about him taking girls home in his younger days but those just stories they heard from the man himself, over the years. I guess they’re true” Charlie shrugged. She smiled genuinely at Y/N. Seeing her new friend happy with one of her oldest friends… her heart could burst with how happy she was for both of them.

“Okay, we need shots” Dorothy said, leaning forward as she flagged down a waiter.

“No, I’m already drinking a Negroni” Y/N sighed, not wanting to mix her drinks.

“One shot’s not gonna do anything” Meg said, as the waiter came over. They ordered four tequila shots, which he left to bring. Once he brought them over, the girls held up one each in a toast.

“Four shots for Y/N’s four orgasms” Meg said, smirking.

Y/N shook her head with a laugh as Charlie and Dorothy laughed, before they all licked the salt from their hands, took the shot and then bit into the limes. Once they were done, they took their regular drinks in hand again.

“There’s one thing that’s bothering me though” Y/N said, frowning slightly.

“What is it?” Charlie asked, confused.

“He uh… he did this last Saturday too, but… he leaves like super early in the morning to do “something”” Y/N replied, using her fingers to air quote ‘something’.

Meg, Charlie and Dorothy all looked at each other, sipping their drinks and not saying anything. Y/N’s frown only got deeper, as she wondered what the hell was going on with them all of a sudden.

“You guys know something” Y/N said as she pointed them out.

“We do… but we can’t say anything” Dorothy said, offering a small smile.

“Dean made us promise not to say anything” Charlie said, shrugging. “But it’s nothing to worry about. Trust us” she reassured her friend.

“Okay…” Y/N trailed off, not really believing them.

“We swear, sweetie” Meg added, taking her hand in hers. “It’s not something to lose sleep over. Okay?”

Y/N looked between her three friends before nodding slowly.

She knew they would never lie to her and she almost immediately felt better about Dean’s mysterious behavior on Saturday mornings, once they told her it was nothing to worry about.

* * *

Dean slid his pool cue forward, watching the white ball hit one of his striped ones into a pocket. Smirking as he leaned up and moved around the table, trying to make the same shot with the next one, but frowning when he missed. Benny stood up after a sip of his whiskey, ready to take his next shot.

“So, how are things going with Y/N?” Sam asked, as he and Cas sat at a four-top table nearby, of the bar they were in. They had both already played a round, now watching Dean and Benny.

“Good” Dean said, simply as he sipped his whiskey.

“Just good?” Sam asked, a small smile on his face.

“Okay… great” Dean smirked, moving to the table when Benny missed the shot. Dean recalled everything that had happened since Y/N got back from New York, minus all the truly sexy details.

“Seems like it’s more than just great, then” Cas said, watching his friends play. “Did you tell her you’re madly in love with her, yet?” he teased.

Benny let out a chuckle as Dean glared at Cas. “Not yet.”

Dean knew it was too soon, and he didn’t think that Cas would ask him that. He hadn’t told anyone that was how he felt, but maybe it was just obvious at this point. Great.

“Why not, brother?” Benny asked, leaning against the pool table.

“Well, I’d rather not scare her away” Dean said, as he leaned down to hit the striped ball. When it fell into the pocket, he went around the table to do the same with another. “I want this one to stick around for a while.”

“Really?” Sam asked, curiously. He felt a little guilty that he hadn’t talked to Dean about this alone first. It was a big shift from Thanksgiving when his big brother didn’t know what to do about his feelings for his neighbor, and now here he was. In a relationship with her.

“Well… yeah” Dean replied, as he moved around the table, closer to Sam now.

“So, it’s serious then?” Sam asked, staring his brother down.

“Yeah, it is” Dean replied, simply.

Sam eyed his brother before a big smile graced his face. Dean shrugged with a small smile, not wanting to make a big deal out of it as he moved back around the table to play the next shot, after Benny missed.

Sam was proud of his older brother; he was finally growing up. Lisa was technically his first serious relationship after Cassie, but he seemed to have matured even more after that experience with Lisa, and was now handling things differently with Y/N. That’s what he picked up from what Dean had told them. Y/N seemed like an amazing girl and really brought out a different side to Dean, something Sam hadn’t seen in him for a long time. He had only met her briefly before she went off to Thanksgiving dinner, but having spoken to Eileen about how much Dean liked her, they had both agreed they would call them over once they got together.

Sam knew then that they had to get to know this girl, now that things seemed serious.

“You should bring her over for dinner tomorrow night” Sam suggested.

Dean stopped and turned, picking up his drink. “You sure Eileen can handle that right now?”

“We’ll keep it simple. Not too late of a night” Sam said, sipping his whiskey. “We kind of already talked about it. If you and Y/N ever got together… we’d call her over to meet her.”

Dean nodded, touched that his brother thought of that already. “Alright, I’ll run it by her. See what she says.”

“Good” Sam nodded, sipping his drink as he watched them continue to play.

“Though… if mom finds out you guys met her first…” Dean joked, just pulling his brother’s leg.

“Crap” Sam muttered, shaking his head. Their mom was going to have a field day when she found out Y/N met Sam and Eileen first.

Dean chuckled as he and Benny continued to play.

* * *

Dean walked into Y/N’s house, smiling as he heard Zeppelin playing softly from the record player. He locked the door, turned the music off and walked down the hallway, smirking as he leaned against the doorframe to her bedroom. She was in her bathroom, going through her nightly skincare routine, the door open. She smiled as her eyes caught his in the bathroom mirror. As she leaned down to wash her face, he walked in and wrapped his arms around her waist. She wiped her face with a small towel and hung it back, then leaned back against him. He leaned down, pressing a kiss to her shoulder, his thumbs grazing along the fabric of his shirt that she was wearing, drowning her as the large article hung off her frame. She had clearly stolen it one day when she was at his house.

“How was your night?” he asked, kissing her shoulder again.

“Crazy, as it always is when Meg’s around” she replied, laughing slightly.

“Yeah, sounds right” he nodded, scoffing a laugh.

“How about you?” she asked, smiling as she packed up her things into a drawer.

“Good” he replied, simply. “I’m happy Sammy could take a night off from ‘lawyering’ to play pool with us.”

Y/N laughed at his use of ‘lawyering’ and turned around, wrapping her arms around his neck as she pushed herself onto her toes. “That’s good.”

“He uh… wants us to come over for dinner tomorrow night” he told her, tentatively, trying to gage her reaction.

“Oh” she said, slightly surprised. “He wants me to come over there?”

“Well, yeah he wants to meet you. Both him and Eileen do” Dean said, smiling slightly.

Y/N smiled, softly as she nodded. “I’d love to meet them, too. It’s just…”

“What’s up, sweetheart?” he asked, concerned.

“I just… I don’t want to say or do the wrong thing. You told me Eileen’s deaf, and I know very little sign language and I just want to make a good impression because they’re your family, and I’m scared that I’ll do something stupid-” she rambled on and on until Dean leaned down and pecked her lips, causing her to stop.

“Okay, first. _You_ … can never say anything stupid. That’s not something you’re even capable of doing, you’re so fucking smart, that it’s not possible. And second… it’s the thought and effort that counts. Eileen will love you, I can guarantee it, and she’ll appreciate you trying. Plus, she can read lips. So, you don’t need to worry about anything, okay?” he explained, smiling reassuringly.

Y/N sighed as she closed her eyes, the nerves only slightly dissipating. “Okay.”

“Hey, look at me” he said, watching her eyes open and meeting his. “I said I’d run it by you but if you don’t want to… I’ll understand.”

She shook her head. “No, I want to. I want to meet your family. So, yes. I’d love to go with you tomorrow night.”

“Awesome” he said, pecking her lips.

“Plus, it’s a good build up to meeting your parents” she shrugged. “Well, just your mom, considering I’ve met your dad, albeit briefly.”

“Yeah, it’s probably better to wait for that” Dean said, laughing slightly. “My mom’s a little… intense.”

Y/N laughed a little as she moved away from him, leaving the bathroom. Dean turned off the light after he stripped down to his t-shirt and boxers. He got into her bed beside her, holding something out. She smiled as she saw a key.

“A key to the house, for you, so you don’t have to keep ringing the bell every time” he said, smirking.

She took it and placed it on her nightstand, taking out another key from her drawer and passing it to him. “Here’s mine.”

Dean placed it on the other nightstand, near his phone. They turned off the lamps and settled in, Y/N cuddling up to him as he wrapped his arm around her.

They made small talk as they both eventually drifted off to sleep.

* * *

Dean knocked three times on the door to Sam and Eileen’s apartment. He looked over at Y/N, smiling reassuringly as he squeezed her hand in his. He was carrying a bottle of wine in his other hand, and she was carrying a covered plate of freshly baked brownies. She had insisted on taking something even as Dean protested that she didn’t need to, and he finally told her that Sam and Eileen both loved brownies. So that’s what she settled on.

“You’re gonna be great, sweetheart” he whispered to her as they waited.

She nodded nervously, breathing out. “If you say so.”

“Wouldn’t say it if it wasn’t true” he smirked, as he leaned over and kissed her cheek. She smiled at him, squeezing his hand in thanks.

The door opened suddenly, Sam on the other side, smiling at them. “Hey! Come on in, guys. It’s good to see you again, Y/N.”

He leaned down and kissed her cheek, and she smiled up at him. “You too, Sam. These are for you guys.”

“Oh god, these smell amazing. Thanks” Sam said, as he took the plate from her.

She looked around the apartment as they walked in, in awe of how open but warm it was. “Your place is beautiful.”

“Thanks” Sam said, as he led them over to the living room. “It’s going to be hard to give it up when the baby is born, but we’ll have to move somewhere bigger, for sure.”

“Congratulations, by the way” she smiled. “Dean told me.” She and Dean sat down on the couch across from Sam, who sat in an armchair.

“Thanks” Sam smiled, bigger now that he thought about the baby.

Just then, Eileen walked in with some corn chips and dip. She quickly put them down on the table as Y/N stood up. She signed “it’s wonderful to meet you” and Eileen smiled, hugging her.

“It’s wonderful to meet you, too” she said, as she pulled away.

Sam took the brownies from the table and walked into the kitchen.

“We’re glad Dean finally got the courage to ask you out.” She playfully nudged Dean as he stood next to her, putting an arm around her shoulders and kissing her head.

“I’m glad, too” Y/N smiled as she looked at Dean.

They sat around and talked for a while, before they moved over to the dining table to eat dinner. They ate, drank, laughed and Y/N couldn’t believe she had ever been nervous to meet Sam and Eileen. They were so welcoming, and she just loved them instantly. As she and Eileen were talking about Eileen’s work as a paralegal, Sam looked over at Dean. He nodded with a smile causing Dean to return the smile. Sam approved and that made Dean really happy. He knew that Y/N would be a great addition to their family, and he knew that his parents would love her too.

Y/N leaned back in her chair, completely content with the evening. The food was great, so was the wine they brought over, but the company was even better.

“That was amazing” she said, putting her cutlery on her plate. “Thank you both.”

“You’re welcome” Eileen said, raising her water with a smile. She looked at Sam, and Y/N smiled as they seemed to have a small conversation between themselves, without even signing to each other.

“So…” Sam started as he sat up in his chair. “We told mom and dad, but we still have to tell you…” He looked at Dean, as he took out his wallet and took out a small piece of paper. He showed it to Dean, whose eyes went wide when he saw that it was a sonogram.

“Hey, look it’s got your wavy lines, Sammy” Dean joked, causing Sam to roll his eyes at the lame joke.

Y/N laughed slightly as she looked over Dean’s shoulder at the photo. Sam pointed out the baby, and she smiled as she watched the three of them get excited about the new addition to their family.

“And… we found out the sex” Eileen said, looking at Dean.

“And…?” Dean asked, waiting not so patiently. Y/N huffed a laugh as she rubbed his arm to calm him down.

“It’s a boy” Sam and Eileen said at the same time.

“I knew it!” Dean cheered as he stood up, hugging Sam when he stood up too.

“Congrats!” Y/N said, hugging Eileen. Dean came over and hugged her, too.

Y/N stepped aside slightly, letting them all have a moment between them. She laughed a little as Dean teased Sam about the kid following in his uncle’s footsteps rather than his dad’s, when it came to profession.

As the conversation changed and Dean and Eileen started to discuss something about her car, Sam moved to clear up the table. Y/N joined him, picking up her plate as well as Dean’s.

“Hey, you don’t have to, Y/N” Sam protested.

“No, it’s okay” she insisted, following him into the kitchen. He started stacking the dishwasher as she passed everything to him. There was a short silence between them, before Sam looked over at her and smiled.

“You’re really good for him” he said, looking over at Dean, who was at the far end of the room with Eileen.

Y/N smiled, softly as she passed him a glass. “He’s good for me, too.”

Sam smiled as he continued to stack the washer. “It’s been a really long time since I’ve seen him this happy. He’s… he’s his old self again. So… thank you.”

“You don’t have to thank me, Sam” she laughed slightly, shaking her head.

“No, I do” he said, firmly as he looked over at her. “For a while back there… I thought he had changed, and not in a good way. You brought out the best in him again. So, yeah… I’m going to be thanking you every day for that.”

He leaned over and kissed her head, surprising her. As he turned away and closed up the washer, turning it on, Y/N smiled.

She felt accepted by Sam and Eileen and she couldn’t wait to be a part of this family. It was still a while away, but she knew that it was on the horizon.

She knew this family was a part of her future.

As Dean drove them home, his hand clasped with hers on the seat between them, he looked over at her and smiled. She smiled back, stroking her thumb over his knuckles.

“You can relax now” he said, looking back at the road.

She nodded. “I am. Though… now I’m nervous to meet your parents. Whenever that happens.”

Dean chuckled, slightly. “Don’t worry, they’re gonna love you, too. You have that effect on people.”

She pressed her lips together, trying not to smile. “Thanks.”

“So… how ‘bout in a couple of weeks?” he asked, looking over at her. “For uh… for my birthday?”

Y/N turned suddenly, smiling wide. “When?”

“The 24th” he replied.

“Of course” she said, picking up his hand and kissing it. Her mind started reeling; ideas coming and going about what to get him for his birthday.

Dean smirked as he continued down the road. Things were finally going right in his life and he owed it all the beautiful woman sitting next to him.

* * *

The sun filtered in through the window, warming the covers of the bed. It was rare for the sun to shine so brightly during the chill of January, but the warmth was welcomed as Dean groaned, stirring from his slumber. He rubbed his eyes as he looked over at the alarm clock, set to go off in another 10 minutes. He ran his hands through his hair, making it stick out in different directions even more than it already was. He smiled as he turned his head, seeing his beautiful girlfriend asleep next to him. He shifted closer to her, leaning over to kiss her cheek and her jaw. She sighed softly but made no move to wake up.

Dean moved his lips down, placing a soft kiss on her neck. He continued to nip at her pulse point, smirking against her skin as she stirred. She blinked a few times, opening her eyes with a sleepy smile on her face.

“What’re you doing?” she asked, with a small yawn.

“Thought we could have a little fun before we have to get up and face another Monday” he replied, mumbling against her neck.

She hummed as she lifted a hand and cupped his jaw. She brought him up to her lips, kissing him softly. The kiss became heated in seconds, as Dean moved on top of her and she moved from her side to her back. Their bodies grinded against each other, his cock getting harder in his sweatpants as she felt herself getting wet.

Her hands slid into his hair, messing it up even more. His hands slipped down under the covers, reaching for the waistband of her pyjamas and pulling them down. She kicked them off as he pulled his sweatpants down. He rubbed his fingers along her folds, feeling that she was wet. He took a hold of his cock and lined himself at her entrance, pushing forward and sinking into the wet canal. He pulled out and pushed in a few times, setting a slow rhythm, as their hips met in a sensual dance.

“Dean” she moaned, looking up at him. “Always make me feel so good…”

He leaned down, kissing her slowly, nuzzling his nose against hers. “You’re so fucking perfect, sweetheart.”

She wrapped her arms around him, bringing him in closer. He kissed and nipped at her neck and collarbone, as he continued to thrust his cock within her. He groaned against her skin as he felt her walls clench around him, fitting around him perfectly as always.

She moaned loudly, feeling her climax approaching, as the muscles in her stomach tightened. “Fuck, Dean… yes.”

His hips became erratic as he was close too. He thrust into her a little harder, wanting to get there at the same time as her. “Shit, Y/N.”

“Cum with me” she moaned in his ear, nipping at his ear lobe as she gripped his shoulders tight.

The damn broke for both of them, as waves of pleasure washed over them. She moaned his name loudly as he growled hers, his cum spurting inside her as it mixed with her slick.

They both jumped in shock as the alarm began to blare through the room, obnoxiously. They laughed as Dean groaned, resting his forehead on hers. He reached his arm over and tapped the button to turn it off. He lifted his head, looking down at her.

“Morning” he mumbled, kissing her once.

“Morning” she smiled, kissing him again. She sighed, frowning as she closed her eyes. “I don’t want to get up.”

“Well…” he smirked, as an idea came to him. “Maybe we can save time and water if we shower together.”

She hummed as she smirked in return. “I like the way you think.”

She wrapped herself around him as he stood up from the bed, his cock still buried inside her. He carried her towards the bathroom, groaning as she clenched her walls around him.

“You gotta stop, sweetheart, or we’ll never get to work” he playfully scolded her.

“You’re the one who suggested showering together” she pointed out, smiling mischievously.

“I did, didn’t I?” he asked, grinning. “Guess I better make it quick then.”

Y/N laughed as he rushed into the bathroom. They stripped off and stood under the stream, the water cascading down his back as he pressed her up against the tiled wall, moving deep within her, pulling sounds out of her that he would never get tired of hearing.

As they both got to work respectively, they were not only relieved that they weren’t late, but also completely satisfied with how their day started.

They couldn’t wait to each other and be completely satisfied all over again that night.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	14. A Lesson in Meeting Family (Part 2)

**Summary for the Chapter:**

> Y/N wants to ensure that Dean has the most amazing birthday, happy to have gotten him presents she really thinks he’ll like. She gives him a great day out, before sucking up her nerves and meeting his parents at his birthday dinner. After, she surprises him by bringing one of his fantasies to life, giving him a completely satisfying, overwhelming and mind-blowing birthday experience.

**Notes for the Chapter:**

> Warnings: Slight angst at the start, some insecurities, mention of reader’s ex, So much fluff, like so much, guys. Happy tears, Laughter. SO MUCH SMUT. Like, so much, guys. Roleplay sex, Rough Sex, Slight Dom!Reader, Slight Sub!Dean, Oral sex (Male and Female receiving), Vaginal Fingering, Unprotected sex (wrap it up before you tap it, people), Dirty talk, Hair pulling, Brief spanking (only twice). And then so much more fluff, again. (I think that’s it lol).

* * *

The next couple of weeks went by quickly, as Dean and Y/N got into a routine of work and seeing each other. They went out a few more times, but they mostly kept to Dean’s house, enjoying their time together, away from the world outside their bubble. They had hung out with their friends, had gone out for dinner a couple of times, went bowling and mini golfing on separate occasions, but it was their time at home that was truly what they enjoyed most.

Y/N had pretty much migrated over to Dean’s. She had brought a few items of clothing over with her, some make-up and some other things that she needed on a regular basis. She had her sleepwear there but most of the time she did steal Dean’s shirts to wear to bed. She only ever went over to her house to get fresh clothes and to do work for school in her home office, so that she would have some time in her own space to concentrate. She loved being there with him, and it had felt like they were practically living together, sparking fantasies in her head of when they would actually move in together.

She had been thinking about the future a lot since she met his brother and sister-in-law. She loved Sam and Eileen and had met up with them on two more occasions since then, as they all hung out with Cas, Meg, Charlie, Dorothy, Benny and Andrea one night at Cas and Meg’s home, and then Dean’s on another night. She wanted to be a part of this for as long as Dean wanted her around, and she hoped he would want her for a very long time. She loved his family; she loved his friends who had become her friends… and she loved him. She loved him more than she ever thought she could love someone.

It scared her to think how quickly it happened, but it also wasn’t scary because who couldn’t love Dean when he was the most amazing person she had ever met? She wanted to tell him how she felt; she wanted to shout it from the rooftops that she was in love, but she knew she needed to wait until it was appropriate to tell him. She didn’t want to blurt it out and ruin everything.

It was a few days before Dean’s birthday, and Y/N had asked Charlie and Meg to meet her at the mall after work. Luckily Meg had worked the morning shift and had the rest of the day off and could join them. She had already gotten Dean what she thought were the perfect gifts for him, but she wanted to do something a little more for him in the form of sexy lingerie. Which is why she had called her girls in for reinforcements. She was going to his parents’ house for dinner with Sam and Eileen coming over too, but once they got home was when she planned to reveal her sexy present.

Y/N was in the fitting room of a lingerie store trying on different sets, as Charlie and Meg sat outside, talking to her. She was glad to have them there, though she had to laugh when Meg had said to just buy anything because Dean would find anything she wore hot and rip it off anyway.

“So, when are you planning to execute the art of seduction?” Meg asked from the other side of the door.

“Once we get back home from dinner at his parents” Y/N replied, as she looked at herself in the mirror, wearing a lacy, light blue bra and panties set. She had told them about her nerves about meeting John and Mary.

“I’m sure that’s going to go great” Charlie said, smiling. “Sam and Eileen already love you, and John and Mary will, too.”

“Yeah, I think so, too” Y/N said, as she unlocked the door.

Meg stepped in and frowned as she saw the color. “Definitely not.”

This was the sixth one Y/N had tried on, after a nude set, light pink, darker pink, red, and then navy blue.

“When in doubt, always go with black” she said, and then gestured to the black number.

“True” Y/N agreed, as Meg moved out and she locked the door again.

She quickly took off the one she was wearing, before putting on the black lacy bra and panties, stockings and garter belt, clipping things in the appropriate places. She opened the door and Meg peered in again, her eyes automatically widening, with a wide grin on her face.

“Oh yeah, that’s definitely it” she said, wagging her eyebrows.  
Charlie came up to them and peered in too, smirking at Y/N in the mirror. “Yeah, take it from me… that’s the one.” She winked at Y/N, causing her to look away shyly.

She cleared her throat and nodded. “Okay.”

Meg and Charlie snickered as they left Y/N to get changed.

After Y/N bought the set and they left the mall, they went to their favorite Chinese restaurant for dinner. Sitting around a round table, Y/N smiled as she looked between these two women who had seen her through so much in the last 6 months. She couldn’t have done any of it without them by her side.

“You guys are so cute together; I can’t deal with it” Charlie gushed as she talked about Y/N and Dean.

Y/N smiled, shaking her head. “I didn’t think I could ever be this happy.”

Meg looked at Y/N knowingly. She knew that look well. “Have you told him yet?”

Y/N shook her head in response, knowing what Meg was asking.

“Why not, Y/N?” Charlie asked, frowning.

“Because… I’m scared something bad is going to happen” Y/N replied, finally revealing her fears. “I’ve had bad break ups in the past, but if anything happened with Dean… this one will end me. I just know it.”

“You can’t think like that, sweetie” Meg said, her usual snarky humour absent for once as she comforted her friend. “It took you guys a long time to get to this place, and everything worked out the way it did for a reason. You’re meant to be with Dean, anyone can see that.”

“I love him so much. I do. I’m just worried I’ll say it too early and ruin everything” Y/N frowned, shaking her head. “God knows I’ve made that mistake before, with Ethan.”

“You’ll know when to say it, Y/N. You will” Charlie reassured her, taking her hand across the table. “This isn’t like Ethan at all; Dean isn’t going to treat you the way he did. He’ll never take advantage of your love.”

Y/N nodded, sighing at her own stupidity. How could she think, even for a split second, that Dean would ever reject her? Every now and then those thoughts that haunted her would creep up, and she had to learn how to keep them in check.

“You’re right” she said, huffing as she shook her head.

“When the time is right… you’ll know it. Trust me” Meg said, a soft smile on her face.

Y/N smiled at her and then at Charlie, squeezing their hands in hers, as they moved on from that conversation once their food arrived.

* * *

The morning of Dean’s birthday arrived.

Y/N was incredibly thankful it fell on a Saturday, making all the executions of her plans that much easier. She had already made him his favorite breakfast of waffles, bacon and fresh coffee as he slept in a while longer. He didn’t schedule to go off on his secret Saturday mission this week, so she had him all to herself on his birthday which she was very happy about.

She had set the table with breakfast and then walked back down the hall to the bedroom. She smiled as she saw him snuggled into her pillow, snoring softly. She walked over quietly, sitting on the edge of the mattress. She reached up and softly combed her hand through his tousled hair, sticking up in different directions. He hummed as he felt her hand in his hair, a small smirk gracing his face, his eyes still closed.

“Morning, birthday boy” she whispered into his ear, as she leaned over him. She slowly climbed up on the bed, her legs on either side of him as she straddled him.

She smiled as Dean turned onto his back, his eyes opening and his smirk growing as he saw her above him. She sat on his hips; her palms pressed into his chest.

“Well, this is a great way to wake up on my birthday” he grinned, sleepily. His hands gripped her hips, stroking his thumbs along the fabric of her pyjamas. She leaned down, kissing his lips softly.

“Happy Birthday, Dean” she smiled.

“Thanks, sweetheart” he smirked as he held her cheek, keeping her close to kiss her again. He tried to deepen it, but she pulled away, smirking.

“Not yet, baby” she said, tapping his cheek as she moved off of him.

Dean frowned as he sat up. “Damn.”

“Don’t worry, I’m all yours tonight” she smiled. “Actually… you’re all mine.” She winked at him, walking out of the bedroom.

Dean grinned as he thought about what that could possibly mean. He got up, brushed his teeth and then met her in the kitchen, walking over to the dining table and sitting down next to her. As they started eating, Dean kept asking her what her plans were, but she wouldn’t budge.

“Not even a hint?” he asked, raising an eyebrow.

“Nope” she replied, popping the ‘p’ as she shook her head. She laughed at his frowny face as she ate. “So… for tonight, should I-” she started asking about what she should bring to his parents, but he stopped her.

“Before you say it, no you don’t need to bring anything” he said, taking her hand in his. “My mom said just bring yourself and that’s it. Trust me, the wine for her and the whiskey for my dad is enough.”

“Well, as long as it’s okay” she said, shrugging.

“It is” he smiled, picking up her hand and kissing it.

She smiled at him as they went back to eating their breakfast.

“Hey, um… I didn’t tell you before but… my dad and I talked. About everything” Dean told her.

“Really?” she asked, curiously. “How’d it go?”

“Good. He uh… he apologized” he replied, nodding as he told her what happened on Thanksgiving.

“Dean, that’s really great” she smiled, leaning over and kissing his cheek.

“Yeah, well… it wouldn’t have happened if you hadn’t encouraged me about the garage so… thanks, sweetheart. I mean it.” he smiled back, squeezing her hand in his.

Y/N couldn’t keep the smile off her face as they continued to eat breakfast. Once they were done, she turned to him with excitement.

“Okay, present number one” she said, as she got up and rushed down the hall.

“One?” he asked, confused. “How many things did you get me, sweetheart?”

She walked in, carrying two large presents, almost as big as the photo of the Impala she had gotten him for Christmas.

“That’s for me to know and for you to find out” she replied, laughing.

He shook his head, feeling a little guilty that she had gone to so much trouble for him. She gestured for him to open it, waiting patiently as he ripped the wrapping off both presents.

“Oh fuck, these are awesome!” he yelled as he looked down at two framed posters of two of his favorite movies: Unforgiven and The Great Escape. He always said he wanted posters for his home office, but had never gotten around to doing it.

“You like?” she asked, smiling.

“I love ‘em” he replied, pulling her into a hug. “Thanks, Y/N.”

“You’re welcome” she said, kissing his cheek. He leaned in and kissed her, passionately.

“Alright, we better get ready because we need to get to present number two” she said, lightly smacking his butt.

“We showering together, too?” he grinned, wagging his eyebrows.

“Nothing’s happening until tonight, Dean” she playfully scolded.

“You…,” he started as he pointed at her. “…are very stubborn.”

She smiled at him, a look of mischief in her eyes as she leaned forward and took the finger pointed at her into her mouth. Dean’s eyes widened as she sucked on it, looking up at him, letting out a small moan as she bobbed her head slightly back and forth. Dean felt the blood rush straight to his dick, feeling himself getting hard. She released his finger with a pop, her tongue running under the length of it.

“Just a preview for tonight” she whispered as she winked at him.

“Son of a bitch” he sighed, shaking his head as he stared at her. She was really going to be the death of him.

She turned and walked towards the hallway, Dean quickly following behind her. She saw him coming up behind her and took off running, straight into the bedroom. She squealed as he always caught her, rushing into the bathroom and shutting the door, locking it. He tried to turn the knob, but he shook his head, annoyed.

“You’re evil, Y/N Y/L/N!” he called out as he heard the shower start to run.

He heard her laughing and shook his head, falling back on the bed. He smiled as he stared up at the ceiling.

God, he loved that woman so damn much.

* * *

Dean and Y/N spent the day out, as she took him to the Automotive Museum’s new exhibit. She had gotten the idea from Sam, who said Dean hadn’t been there since he was a kid with John. She found out the museum had a new exhibit on classic cars and knew she had to take him there. She couldn’t stop herself from smiling as she saw his excitement as they made their way through the exhibit. He was a kid in a candy store, and she had fallen in love with him all over again. They went for a quick, light lunch after they left the museum, before they returned home. They spent a few hours relaxing on the couch, watching TV before getting ready to go for dinner to his parents’ house. Y/N got ready at her house, not wanting Dean to see the lingerie she had put on under her pink A-line dress and brown knee-high boots. She put on her black coat and scarf, picked up present number three and her purse, before leaving her house.

Dean was waiting outside his house with the bottles of wine and whiskey and smiled when she walked over. He shook his head as he looked at yet another big present, though not as big as the others.

“You have a problem, sweetheart” he laughed.

“I’m just making this day special for you” she said, smiling as she sat in the car.

As he started the car and pulled out of the driveway, he glanced over at her as he drove.

“You’re making me look bad, Y/N” he said, looking out at the road ahead of him. “I only got you a record.”

She cocked her head to the side, shaking her head. “We weren’t together then, Dean. It’s totally okay. Plus, even if we were, it’s the thought that counts. So, I don’t care if you get me 50 things, or just one thing… I’d love it all the same.”

He smirked, picking up her hand and turning his head, kissing her knuckles. He kept their hands connected as he drove with the other towards his parents’ house.

Once they got there, Dean parked outside on the curb behind Sam’s car, taking Y/N’s hand as they got out of the car and walked on the cleared path up to the porch. She carried the whiskey for his dad, and he carried the wine for his mom. She smiled as she admired the modest clean white lines of the house, a porch swing on the porch as well as hanging plants. Dean rang the doorbell and she let out a deep breath.

“You got this, sweetheart” he whispered as he looked at her.

She nodded with a small smile, gripping his hand tighter as the door opened to reveal Dean’s dad, John, on the other side.

“Hey, kids” he smiled at them as he opened the door wider to let them in. “Happy Birthday, Dean.” He hugged Dean; Y/N quickly dropping her hand from his so they could.

“Thanks, dad.” Once they pulled away, Dean turned to her and smiled.

“Good to see you again, Y/N” John said, offering his hand with a smile.

She took it, shaking it as she felt herself relax. John was a lot like Dean, relaxed and carefree, and she could tell that from their first meeting, too. “Good to see you again, Mr. Winchester.”

“Again?!” they heard a voice call out from behind them. They all turned to see Mary walking over, wide eyed. “You’ve met her before?”

“Honey, it was just for a minute or so, a couple of months ago” John explained, getting Mary to relax.

“Mom, it was barely a meeting” Dean added in. Y/N looked nervous and he wrapped his arm around her, his thumb stroking her shoulder.  
Mary frowned before she shrugged. “I’ll allow it.” She looked over at Y/N and smiled, and the younger woman felt herself relax a little again. “It’s wonderful to meet you, Y/N.”

She leaned in and hugged Y/N tightly. Y/N tried to keep the smile off her face, but she couldn’t.

“You too, Mrs. Winchester” she said, as they pulled away.

“Oh sweetie, please call us John and Mary” Mary laughed, as she led them into the living room.

“Okay” Y/N laughed, slightly more at ease. She held out the whiskey and wine. “These are for you.” She handed them over respectively and got little looks of approval with a thanks from each of them.

Mary turned to her son and enveloped him in a tight hug. “Happy Birthday, my beautiful boy.” She kissed his cheek, causing Dean to grimace slightly. The display of motherly affection in front of his girlfriend was a little embarrassing. She found it cute though.

Y/N greeted Sam and Eileen, and Mary glared at all of them when she realized that they had all met before too. “Alright, that’s it. I’m the only one talking to Y/N tonight.”

She linked her arm with Y/N’s as they sat down on the couch. She looked over at Dean and he just looked at her with a “I told ya so” look.

“What’d I tell ya…” he gestured to the women’s linked arms with his finger. “Intense.”

Mary asked Y/N every question possible about her life back in New York, her family and teaching and Y/N answered as articulately as she always did. Dean watched her with a smile on his face. He could listen to her all freaking day. Once they all sat down to eat, Y/N listened happily as they reminisced about their family holidays, past birthdays and the boys when they were younger.

“And it’s just a mess! It’s greasy, and fatty and I just can’t believe I ever fed that to them!” Mary laughed, as she recalled the first dish she ever made for John and Dean when they all moved into the house.

“But wait” Y/N stopped them as she tried to stop laughing. “Why is it called Winchester Surprise?”

“I really don’t know” Mary said, her laughter calming down into a giggle. “It was a bunch of things mixed in together… so, surprise!”

Y/N shook her head as she calmed down, looking over at Dean who had calmed down as well. Dinner was absolutely amazing and so was everyone else. John and Mary were warm and welcoming, and she couldn’t believe how well she fit in with everyone. It was overwhelming and her heart was completely full.

“But he just loves it, for whatever reason” Mary said, gesturing to Dean.

“It’s so gross” Sam chimed in, shaking his head as his face scrunched up in disgust.

“Yeah, you would think that, health freak” Dean teased.

“Shut up” Sam hit back, a typical younger brother response.

“I have to be honest, I like it too” Eileen confessed, with a sheepish smile.

“I knew I liked you for a reason” Dean smirked as he pointed at her.

“I’ll have to try it sometime” Y/N added, smiling at him.

“You should” John said, nodding.

“Dad made it once… well, tried to anyway” Dean laughed. John joined in, shaking his head.

“God, that thing was… now, that was disgusting” John said, still laughing.

Mary quickly got up and walked into the kitchen. She returned with a big pie with several candles around it, all lit.

“Okay, 1… 2… 3…” She counted before everyone started singing ‘Happy Birthday’ to Dean. She placed it in front of him and smiled softly the whole time as he looked around at everyone.

Dean’s eyes landed on Y/N, who smiled brightly at him as she sang. If someone had told him last August that he’d break up with Lisa and be with this incredible woman who encouraged him, who looked out for him and who fit in so well with his family, he would think they were insane. He didn’t think he’d ever feel this way for anyone, so completely content. He was a lucky man. He knew he was.

Dean blew out the candles and made an actual wish, for the first time in a long time. He wished for this woman sitting next to him to always be there. To always be with him, through every obstacle that would no doubt come their way. He knew together they could conquer anything.

* * *

After dessert, Dean watched from the kitchen as Y/N sat with John, Sam and Eileen, chatting with all of them. He smiled as he saw her trying to learn a few more phrases in sign language from Eileen. He found it comical that she had ever been scared that she wouldn’t be able to handle meeting his family. She was amazing and they all loved her. He couldn’t be happier about that.

“So, when are you dropping the big L-bomb?” Mary asked, as she suddenly came up next to him.

“What?” he asked in return, confused.

“Dean, come on” Mary said, raising an eyebrow.

Dean looked at his mom, sighing. He knew he couldn’t keep things from her; she was too good at figuring stuff out.

“I don’t know when” he shrugged.

Mary hummed, leaning against the bench next to him. “Might I suggest… soon?”

Dean folded his arms across his chest, nodding. “I’ve… I’ve never really said that to a girl before.”

“Okay” Mary nodded, slowly. “But… that is what you feel, isn’t it?” She wanted to make sure that she was reading things right.

“Yeah” Dean nodded, firmly. “It is.”

“Then, follow your heart, Dean” she told him, as she placed a hand on his arm. He looked at her, seeing her smiling at him. “You found her, and you found what you want. So… just don’t worry about anything else. It’s all going to be okay, sweetie.”

Dean shook her head. “But what if-” he started but she shook her head, cupping his cheeks in her hands, making her look at him.

“No, Dean. No what ifs. There’s going to be a lot of things that come your way; some good, some bad… but they’re going to pass, too. They’ll pass because you have each other, because you’ll get through it all, together” Mary explained, her eyes glistening with unshed tears. “All you have to do is try. Just follow your heart… nothing else.”

Dean nodded, firmly as he looked at his mother, hearing her words clear as a bell.

“Thanks, mom” he said, leaning in and hugging her tightly.  
“I just want you to be happy, Dean” she whispered as she hugged him. “And from what I’ve seen tonight… I’ve never seen you happier.”

Dean pulled away from her, trying to keep the huge smile forming away from his face. It broke through as he chuckled. “She… she makes me happy, mom. She really does. She… she makes me wanna be a better person.”

“She’s wonderful” Mary smiled.

Dean smiled as Mary did too, squeezing his shoulder as she walked past to make coffee for everyone.

Dean turned and saw Y/N wave him over. He walked over and sat down next to her, smiling when she handed him his next present. She smiled brightly, giddy for him to open it. He placed it on the coffee table and tore the wrapping back completely, his eyes widening when he saw what was inside. It was an old black and white photo, blown up and restored, of his grandmother Millie Winchester. She was standing outside the garage which looked much different back then than it did today, standing in front of an old car, shaking hands with a customer. It looked to be a photo from the 60s, the car looking around the same time as well.

“I had a little help with this one” she said, as she winked at Sam. Dean looked between her and his brother, both of them smiling at him. “I thought you could put it up at the new site in the reception area. It would a great place to do a history of the business.”

“Y/N…” he trailed off, still staring at the photo.

“Sam asked your dad for that photo because… well, the photo is from 1961 but that car is a 1958 Impala. The first year of the Impala, to be exact” she explained, a big smile on her face as she gaged his reaction.

Dean looked up at her and then looked at his family. His mom smiled at him, seeing that he was overwhelmed by the conversation they just had and now this beautiful gesture.

“This- I…” Dean couldn’t from words. He was completely speechless. Just when he thought she was done making him fall harder for her, she did this. Just another reason to fall madly in love with her all over again.

“Why don’t we give them a minute?” Mary suggested. Everyone filed out of the room, John squeezing Dean’s shoulder as he walked past.

“Dean?” Y/N looked at him, trying to look into his eyes to see if she could figure out what he was thinking.

Suddenly, he cupped her cheeks in his hands and pulled her in, kissing her, passionately. The feverish kiss left her breathless as he pulled away, his brilliant green eyes staring into her Y/E/C ones.

“I love you.” The three words he had been wanting to say to her spilled out of him easily. No pause. No hesitation. There was no need for all of that when she made loving her so easy.

Y/N was shocked, but her face morphed into happiness, her smile beaming brighter than ever. “I love you, too.”

Dean smiled and she honestly felt like it was the most beautiful sight she had ever seen. He leaned in, kissing her again, his hands cupping her jaw, his thumbs softly stroking her cheeks. She held onto his wrists as she melted into the kiss, not wanting to stop.

Dean did pull away, however, to look down at the photo. “Y/N… this is freaking amazing. No one’s… no one’s ever done something like this for me. Thank you.”

She leaned over, kissing his cheek as he looked down. “Don’t mention it.”

He tilted his head, resting it against hers. They closed their eyes, basking in the feeling of what they just confessed.

They couldn’t see, but everyone was peeping out from the kitchen, watching them with huge smiles on their faces. Mary and Eileen were clinging to each other, practically bouncing off the walls with giddiness. Luckily, Dean knew his family pretty well.

“You guys can come out now” he said, lifting his head and turning it slightly in the direction of the kitchen.

Y/N stifled a laugh as she watched everyone walk out, looking sheepish.

Soon after, Sam and Eileen left when she started feeling too tired to stay. Dean and John were discussing something to do with the garage, as Mary continued to clean up. Y/N walked into the kitchen, smiling when Mary looked up at her with one.

“Anything I can help with?” she asked as she walked in.

“No, absolutely not” Mary replied, shaking her head.

“Mary, please-” Y/N started but stopped when she received Mary’s stern mom face.

“Y/N” she playfully warned.

“Okay, okay” Y/N laughed as she held her hands up, sitting at the island on a stool. She quietly watched as Mary put dishes away in their respective areas.

“Thank you” Mary said, looking up at her. “I’ve been meaning to say it since Dean walked in the door looking happier than I’ve ever seen him. So… thank you.”

Y/N smiled; it seemed like she couldn’t do anything else but that when it came to Dean and his family. She had never felt so welcomed before, and the fact that she fit right in with them just meant that she and Dean were meant for each other.

“He’s a wonderful man” Y/N said, as she thought about Dean. “Everything he’s done for me… I’ll never forget it. He’s incredibly kind and sweet… so I have to thank you for that.”

Mary glanced at her, smiling, before she went back to what she was doing. “For a while there… I didn’t think he’d find someone. I’m very glad he did.”

“Can I ask you something?” Y/N said, curious about the answer to her next question.

“Sure” Mary nodded.

“Does it worry you… the age difference, I mean?” Y/N asked, worriedly.

Mary was quiet for a moment, before she shook her head. “No. It seems like a lot… but 7 years isn’t a big deal. You’re good for him; a lot of women his age haven’t been.”

Y/N nodded. “Okay, good. I was worried for a minute… that you’d think I’m too young or something.”

“You are a little young…” Mary laughed, slightly as she turned to Y/N. “But I can see how much he loves you. So, age doesn’t matter in the grand scheme of things.”

“Thanks, Mary” Y/N said, relieved.

Mary stopped what she was doing suddenly, her head ducked down as she shook it. “I’ve been so scared for him. He drifted for so many years. I thought Lisa was going to be good for him, but it just broke that spirit that he had. Now you’re here… I’m not scared anymore” Mary looked over at her, her eyes glistening with tears. “You brought that spirit back.”

She reached across the surface of the bench and clasped Y/N’s hands.

“Mary… I love your son” Y/N told her, shedding a few tears herself, feeling them roll down her cheeks. “I promise I’ll never hurt him.”

They smiled at each other through tears, their hands still clasped.

Dean and John walked in, chatting casually when they both stopped as they saw the women in the kitchen. Dean looked between his mom and Y/N, wondering what the hell he just walked in on.

“Everything okay here?” he asked. He watched as their hands unclasped, reaching up to wipe under their eyes.

“Fine” they both said, as they wiped away the evidence of their emotional display.

“What did you do?” Dean asked his mom, suspiciously. He knew what they walked in on definitely had something to do with his mother.

“Nothing” Mary shrugged.

“Uh huh” Dean muttered, not believing her.

“You’ll never get it out of her, son” John tapped him on the back as he walked into the kitchen. Y/N laughed a little as Dean shook his head.

They left soon after, Y/N thanking John and Mary for welcoming her in. She promised Mary to have lunch with her sometime soon, before they got into the Impala and went home. Dean pulled into his driveway and shut the car off. He leaned over and kissed Y/N, leaning his forehead on hers once he pulled away.

“Thank you for today” he whispered.

“It’s not over yet” she smirked, a twinkle in her eye as she lifted her head and looked at him. “In fact, the night is still young and I have a lot of plans for us.”

“Oh yeah?” he smirked, raising an eyebrow.

“Yes, but first…” she leaned down to her purse and opened it, taking out an envelope. She handed it to him. “Open present number four.”

Dean stared at her as he shook his head. “You’re too much, sweetheart.”

“Oh hush, just open it, come on” she dismissed his comment, tapping his shoulder several times as she grew impatient for him to see his next present.

“Alright, jeez” he groaned, laughing slightly. He opened the envelope and took out two things that looked like tickets. His eyes widened as he read them.

“Iron Maiden tickets?!” Dean looked up at her, beaming. “When?”

“In May” she replied, happily. “You like?”

“Are you kidding me, sweetheart? This is fucking awesome!” He pulled her in, hugging her tightly. He let her go and kissed her again.

She pulled away too quickly for him, however, as she gathered her purse. “Okay, you put those and the photo away, and then meet me in my office in 20 minutes.”

He looked at her, a frown forming on his face. “What’s going on?”

She winked at him but didn’t say anything. He shook his head, leaning in to kiss her. He tried to deepen it, but she pulled away again.

“If you want present number five, you better do what I say, Dean Winchester. Don’t be a bad boy” she playfully warned him.  
“I thought you liked me when I’m bad” he grinned, wagging his eyebrows.

She felt the heat rise up in her cheeks and the rest of her body, but she had to keep calm if she was going to execute her plan properly.

“I do, but…” she leaned over, her face close to his as she stared down at his plump, sinful lips. “You’ve been a good boy today and you deserve a reward from Miss Y/L/N.”

Dean huffed as he felt the heat in him radiate throughout his body. “How many gold stars do I get?”

“All of them… if you’re good and get to mine in 20 minutes” she said, playfully stern as she moved away from him.

She got out of the car and smiled at him one last time before she walked across the street. Dean watched her go into her house and close the door.

“Fuck” he whispered to himself, the smirk never leaving his face.

Y/N quickly stripped out of her dress, leaving her lingerie on as she went to her closet and put on a short, tight, black skirt and a white button up shirt which she tied at her waist, exposing her stomach and leaving the top open to show off her bra, and rolled up the sleeves to her elbows. She took off her boots and put on her black heels, before she strutted into the bathroom to fix her make-up and applied red lipstick. She pulled her Y/H/C hair up and made it into bun, leaving a few strands of hair to frame her face. She walked out of the bathroom and picked up her purse, taking out her red glasses. She put them on and turned to her full-length mirror, smiling at her handiwork.

Dean didn’t know what was about to hit him.

She went into her office and fixed up the desk, making sure nothing important was on it. She glanced at the clock and smiled, as it just hit twenty minutes. She leaned against the desk, picking up her large ruler which she picked up from the spare supplies at school, and held it against her shoulder.

She smiled to herself; she couldn’t wait to see Dean’s reaction.

* * *

Dean had been too excited to see what the next present was, that he practically sprinted across the street when his twenty minutes was up.

He unlocked the door and walked into her house, locking it behind him. He shrugged his jacket off and took off his scarf and hung them by the door, walking down the hallway. Y/N had said to meet in her office, so he headed that way, his boots echoing on the floorboards.

“Okay, sweetheart-” he started to say as he turned into the office but stopped short very quickly as he saw Y/N. His mouth fell open as he gawked at her, and he instantly felt blood rush to one area within his jeans. He took her in, looking like she had walked right out of a porn video or his dreams and into his reality.

“Right on time, Mr. Winchester” she said, seductively.

“Fuck, Y/N” he started as he walked over to her, but she extended her ruler, pressing it into his chest to keep him at a distance.

“Nuh uh, no bad language in my class. And you’ll address me by my last name” she warned him, taking her role very seriously.

Dean tried not to look so giddy, but he was bursting at the seams. “Yes, Miss Y/L/N.” He choked it out, feeling his jeans tighten as his erection grew just by seeing her this way. She was always beautiful, and he always found her incredibly hot, but this was just another side to her that he was very happy to enjoy.

“Now, you’ve been a very good boy, Dean” she said, smiling seductively. She walked towards him, lifting the ruler off him as she grabbed his shirt. She guided him around, his feet shuffling along the floor, until he rested against the desk. “And you deserve something from me.”

Dean couldn’t do anything but stare at her as he nodded. She put the ruler down on the desk and winked at him as she crouched down, her knees pressing into the floor of her office. She looked up at him as she rubbed her hand over the crotch of his jeans and felt his hard on, chuckling a little as Dean jerked at her touch. She unbuckled the belt and pulled it through the loops, throwing it somewhere in the room. She undid the button and zipper, pulling the jeans down his legs, bunching them at his ankles. She reached for the waistband of his boxers and pulled them down, smirking mischievously as his cock sprang free.

“Take off your shirt” she instructed him as she looked up at him. Dean obeyed as he undid his thick black and white flannel shirt and took it off, followed by his white t-shirt, exposing his hard yet soft torso to her. Her hands moved up his stomach, feeling the muscles twitch under her touch. They came back down slowly, her eyes never leaving his. She took a hold of his cock in one hand, slowly beginning to pump her hand back and forth along the shaft. She saw pre-cum leak out from the tip, and leaned forward, licking it off as she swirled her tongue around the head.

“Fuck” he sighed as his hand reached her head to hold her hair. She instantly grabbed it and the other one and planted them both on the edge of the table. She shook her head, her mouth right near his cock. “No touching or I’ll stop.”

Dean clenched his hands around the edge of the desk, not happy that he couldn’t move them. Y/N leaned in again, sucking the head into her mouth, as she swirled her tongue around it. She moved her mouth further, feeling him sink in inch by inch, until he hit the back of her mouth. She drew back and then moved in again, bobbing her head slowly as her hand massaged his balls.

“Oh fuck, sweetheart” he groaned, wanting desperately to touch her.

She looked up at him in warning for using that word, before she continued. She bobbed her head, saliva slicking his shaft as she continued what she was doing. His cock hit the back of her mouth repeatedly, testing her gag reflex. She held him there for a moment, drawing back to breath as she pumped his throbbing cock with her hand.

“God, Y/N… no, damn it, Miss Y/L/N” he corrected him through his pleasure, and she smirked as she continued to move her hand.

“How does my hand feel, Dean?” she asked, moving faster and causing him to moan loudly.

“So good, Miss… so freaking good” he replied, looking down at her through hooded eyes.

“What about my mouth?” she asked before she took her hand off and took him into her mouth again, bobbing her head in a quick rhythm.

“Even better” he growled, his nails scraping into the wood of the desk as his hands clenched.

She pulled off him, laughing. “You’re behaving very well, Dean. Maybe it’s time for another reward.”

“Yes, please Miss Y/L/N” he said, biting his lip.

She quickly stood up, giving him a few seconds to remove his boots and then take his jeans and boxers off completely. She moved him to stand in front of her as she leaned against the desk. She pulled her skirt up slowly, revealing her thigh-high stockings attached to a garter belt and her matching thong. She pulled the thong down, kicking them off her heels. She sat back on desk, lifting her leg onto the desk and exposing herself to him. Dean’s eyes darkened as he saw her pussy, her wet slick shining on her skin.

“On your knees” she commanded.

Dean smirked softly as he bent down, her pussy level with his mouth. She shifted forward and combed her hand through his short spikes, pulling him forward until his mouth was on her folds. He immediately began to lick her folds, feeling her wetness coat his tongue. She gripped his hair tighter, throwing her head back.

“Oh fuck, Dean… you’re so good at that” she moaned loudly. Now that they were at home, they didn’t have to worry about not making a sound, and she couldn’t have been happier to fully express her enjoyment.

“You taste so good, Miss Y/L/N” he told her, as he moved up to circle his tongue around her clit. He swirled his tongue around the bundle of nerves, making her cry out.

“Oh Dean, yes! Just like that, don’t stop. Use your fingers, too” she whimpered, pushing her glasses up the bridge of her nose as they slipped.

Dean added two fingers, thrusting them in and out in a fast motion, the pads of his fingers running along her walls and hitting her g-spot with every thrust. She clenched her walls around his fingers, as she began to move down on them.

“Good boy, oh you’re such a good boy for me, Dean” she praised him as she gripped his hair tighter. “I want you to fuck me now, fuck me with that big cock of yours.”

Dean instantly removed his mouth and fingers, standing up. He reached for her shirt but looked at her, silently asking for permission. She smiled approvingly and nodded. He quickly undid the knot and pulled the shirt off her, seeing her bra. He reached behind her and unclasped it, watching as she let it fall away down her arms. Dean moved closer to her, holding onto her hips. She smirked at him, lifting her left leg and placing her calf on his shoulder.

“Shit” he groaned as he watched her, holding onto her tighter.

He pumped his hand along his cock a few times, slapping it against her clit. She moaned and cupped his jaw, pulling him into a rough kiss. He held himself at her entrance, pushing into her in one swift motion. She pulled away from the kiss, crying out as she felt him inside her. He immediately began a fast rhythm, pulling out and pushing back in, thrusting hard.

“Yes, just like that” she gasped, her hips meeting his at the same pace. The desk began to shake with the force of their actions. “Fuck me hard, Dean.”

Dean grunted as he gripped her leg, angling his hips to thrust into her deeper. “Fuck, you feel so fucking good, Miss Y/L/N. So perfect.”

She reached her hand down to one globe of his ass, striking him twice in quick movements. He let out a strangled noise at the shock of her doing that.

“Language, Dean. Do you want me to spank you more?” she said, cupping his jaw with her other hand and making him look at her.

“No, Miss Y/L/N… I’ll be good” he said, a slight smirk on his face.

“Wipe that smile off your face, young man. I don’t like that attitude” she said through her moans.

“Sorry, Miss Y/L/N” he groaned.

“Your cock feels so good inside me” she moaned loudly, staring into his eyes. “Love the way it feels, making me feel so full. How does my pussy feel, baby?”

“So tight, Miss Y/L/N… so wet… so good” he grunted, his voice gravelly and turning her on even more.

“You love it, don’t you?” she asked frantically, feeling herself getting close.

“Yes” he choked.

Y/N laughed a little as she took him in. His eyes hooded and skin flushed as he fucked her. He had never looked or sounded more submissive than he did now, and she felt herself grinning as she thrust down harder on him; her plan very well executed.

Dean could feel her walls clenching him tightly and knew she was getting close to her climax. He dropped her leg off his shoulder and pulled her tight against him, her breasts pressed into his chest as they stared into each other’s eyes.

“I want your cum inside me, Dean. I want you to cum deep inside me, fill me up, make it drip out of me for days” she told him, staring intensely at him.

“I want that too, Miss Y/L/N. I wanna cum” he groaned, his hips getting more frantic as he neared his own release.

“Cum with me, Dean. Cum with me, baby” she moaned, holding him tighter.

He didn’t say anything else as he let out a strangled groan, his neck strained and veins popping as she threw her head back, letting out a small scream as they cum at the same time, their release mixing together inside of her.

“Fuck” he laughed, as he leaned his head on her shoulder, shaking his head and breathing heavily.

She laughed lightly, combing her hands through his hair.

Dean lifted his head and looked at her, as he breathed deeply. He couldn’t believe she was real. Of all the things he had done with women, that was the first time he had done that. Let someone dominate him. He always took charge in bed, only occasionally letting go of the reins, but this was the first time he completely let go and trusted someone else to take care of him. She was truly something special, and he made a mental note to let her do it again sometime soon. It wouldn’t be a regular thing because he loved to be the one who was in control in bed, but she was a dirty girl with a dominant side, and he was very glad to discover that about her.

“That was…” he shook his head, not being able to summarize how brilliant that experience had been.

“I know” she said, knowing how he felt without having to say anything.

“You…” he started, his breathing coming back to normal slowly. “are fucking incredible.”

“So are you” she countered, but he shook his head.

“No, that was something else” he huffed, not knowing what to say because his brain had been turned into mush. “You’re something else.”

“I’ve… that was the first time I’ve done that, properly at least” she confessed. “I just wanted to do something different for your birthday.”

“Well… thank you” he said, smirking. “And you’re going to be doing it more often.”

She felt the heat rise in her cheeks, hiding her face in his neck. He moved away not letting her hide after that display of dominance.

“Don’t you hide now, sweetheart. Fuck, that was so hot” he grinned, leaning down and kissing her, hard on the lips.

Neither of them bothered to redress, as Dean carried Y/N into her bedroom. It felt weird to be there after pretty much being at Dean’s for so long, but they didn’t think too hard about it as they got under the covers. She turned her speaker on and let one of her playlists play softly in the background.

“So…” she started as she traced random patterns across his bare chest with her finger. “Who gave you this teacher fantasy you have?”

He laughed loudly, shaking his head. “I can’t believe you figured it out.”

“I had it figured out since I told you I was a teacher the first time I met you. And then you got to the school so fast that night we had sex there… you’re not subtle, Dean Winchester” she teased him, kissing his cheek.

“Yeah well, I’m glad you did” he said, kissing her nose.

“So, tell me… who?” she asked again. She looked up at him, trying to supress a giggle as she saw his cheeks flush pink.

“Uh, Mrs. Sullivan. 10th grade Biology. She was… she was pretty hot, I-I had a crush on her but then she left after she got divorced” Dean replied, stuttering slightly.

She laughed a little, finding him so cute in that moment. She leaned over and cupped his jaw, kissing him softly.

“You’re so adorable” she smiled, totally enamoured by him.

“Yeah, I am” he agreed, a smug smirk on his face. He laughed as she shook her head but loving the feeling of his laugh rumbling in his chest under her hand.

“See… not subtle” she muttered with a smile.

“Yeah, but you love it” he said, as he turned his head to look at her as she rested hers on his shoulder.

“I do” she whispered as she looked up at him. “I love you.”

“I love you, too” he said, as he leaned his forehead against hers. “Thanks for a great birthday.”

“I’m glad you enjoyed it” she said, snuggling into him. She smiled as _Feel Like Makin’ Love_ by Bad Company started to play.

“Best in a long time” he told her, kissing her forehead.

She looked up at him and pecked his lips in a small kiss. “Well, there’s still an hour and a half until it’s officially over. There’s plenty more we can do.”

_Baby, when I think about you_

_I think about love_

_Darlin’, couldn’t live without you_

_And your love_

_If I had those golden dreams of my yesterday_

_I would wrap you_

_In the Heavens_

_And feel it dyin’ (dyin’) all the way_

Y/N climbed on top of Dean, straddling him as laid on his chest, kissing him passionately. His hands ran down her smooth back, over her ass and held onto her hips. She smiled into the kiss as she felt his already hard cock press against her behind. She shifted back slightly, and took hold of cock, lifting her hips up and pressing him into her heat. She moaned against his lips, as she began to move on top of him in a languid pace. Dean’s hips moved up to meet hers, matching the pace of her thrusts. He sat up with her in his lap, wrapping his arms around her as hers wrapped around his neck, their lips never breaking the kiss. She gasped, pulling away from the kiss and looking into his eyes.

_I feel like makin’_

_Feel like makin’ love_

_Feel like makin’ love_

_Feel like makin’ love_

_Feel like makin’ love to you_

Dean had seen various versions of her today. He saw the Y/N that wanted him to have a great, fun day, taking him out to see a car exhibit. He saw the Y/N that met his parents, smiling brightly as she fit in so well with them. He saw the Y/N of his sexual fantasies, the dominant side he didn’t know she had but couldn’t wait to explore further. And now… he saw this Y/N. The one who had eyes only for him. The one who loved him unconditionally and gave herself completely to him. The who trusted him without a doubt in her mind.

And that Y/N was the most beautiful of them all.

They moved against each other, continuing the same rhythm they had started. As the crescendo of the song playing from Y/N’s speaker hit, they both picked up the pace and quickly felt themselves reaching the edge of the cliff. The only sounds heard in the room apart from the music were their soft moans and grunts as they reached the peak of ecstasy together; holding onto each other as tightly as they could, calling out each other’s names for only them to hear.

Soon after, once they had come down from their high, Y/N fell asleep curled up against Dean. He watched her with a smile on his face, admiring her peaceful face as she slept. In that moment, he couldn’t help but believe in some kind of higher power, because he had clearly done something right to be rewarded with this woman.

Whatever it was, he was incredibly grateful for whatever had decided to look down on him and grant him everything he could ever want.

**Notes for the Chapter:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


	15. A Lesson in Finding The One

**Summary for the Chapter:**

> Dean and Y/N find themselves so busy in the following weeks, that things blow out of proportion and they spend the night apart. Feeling awful about it the next day, they plan to apologise to each other but something unexpected stops them from that. Later, Dean and Y/N share a tearful apology, after the experience of nearly losing each other makes them realise what is truly important.

**Notes for the Chapter:**

> Warnings: Swearing, Angst, Fighting, Hurtful words, Doubts, Insecurities, Guilt, Tears, Hurt!Dean (don’t hate me, it’s not for long), Hospital, Tears, Fluff, Romance, Smut, Oral sex (Female receiving), Dirty talk, Vaginal Fingering, Brief handjob, Unprotected sex (wrap it up before you tap it, people), A whole bunch of fluff.

* * *

Two more weeks passed that were incredibly busy for both Y/N and Dean.

Dean had been swamped between the old and new sites, trying to fix up people’s cars at the old and then working with Benny on the car that had come in for restoration at the old site, but they moved it to the new. They had gotten this big job a few months ago, and had started then but moving it over to the new site had been a good decision as everything was more open and had more room to move around. They had so many people calling in with every model of car Dean had ever heard of, in different states and different forms of restoration that needed to be done. There were only so many they could book, and had to eventually tell people they couldn’t take any more for the next few months.

He had been coming home later and later, and barely had time to even kiss Y/N let alone do anything else. He really couldn’t wait until they hired a few more people and he could finally go back to his regular hours. They were in the middle of the hiring process too; yet another reason they had been so busy.

Y/N had a lot going on at school as well. There had big tests she had given her students in both grades and had a lot of grading to do. While that was happening, she also had to plan lessons for the new content they had to cover, while also taking on a few tutoring duties after school for the kids that really needed help, in order to get to the high school level by September.

She had been coming home later than usual, but then she would cook and leave something for Dean to eat so that when he came back late, he wouldn’t come to bed absolutely starving. She had barely seen him, always falling asleep before he got home because she was so exhausted herself.

She really hoped things would slow down soon for both of them so that they could have more time together.

Y/N was in the middle of grading tests when she heard the front door open and close, and then Dean’s boots in the hallway. She usually did her work in her office at her own house but considering she had just made a quick and easy pasta for dinner over at Dean’s, she decided to sit at the dining table after eating and grade the papers there.

“Hey, sweetheart” Dean muttered as he saw her, sounding completely wrecked.

She looked up at him, offering a small smile. “Hey. Food’s still hot, so eat up.” She went back to her grading as she heard him wash up and then sat down with his food, across from her at the table.

“How was your day?” he asked, taking a bite and looking at her.

“Busy” she replied, not looking up from the tests in front of her. She pushed her glasses up as they slid down her nose but made no move to look up at him.

Dean frowned as he saw her so engrossed in her work that she didn’t even look at him. He really wanted to take a few minutes to just be with her, considering they had barely talked in the last two weeks.

“Y/N, can’t you put that away for a while?” he asked, trying not to sound too frustrated.

“No, I can’t, Dean. This is important; I’ve been so behind with grading, and the kids are really getting antsy about their scores” she replied, shaking her head as she continued to look down.

“Sweetheart… we’ve barely seen each other. You can finish that in the morning too” he countered.

“I’m almost done, Dean. Please, just… let me finish. You can keep talking, I’m listening, okay?” She was irritable and really hoped he wouldn’t push any further.

“Yeah. Okay” he mumbled as he continued to eat. “Maybe… maybe we can go out on Friday night. God knows we haven’t been out, just us, in a long time.”

“We really don’t have to” she said, quickly glancing at him before continuing her work.

“Oh, come on, Y/N. It’ll be good, we can finally relax” he said, smiling slightly, hoping she’d look up at him and actually agree.

She scoffed as she shook her head. “Yeah, and then you can leave me in the morning like you always do for your top-secret mission.”

An eerie silence fell in the house as Dean stopped eating. He put his fork down slowly as he looked at her. He kept calm as he thought about how to broach this.

“What’s that supposed to mean?” he asked, calmly even though he was a little annoyed.

She finally looked up at him with her glasses on, and if it was any other day, Dean would’ve found it incredibly hot rather than scary. “It means that there’s no point in us going out on Friday night if you’re just going to leave the next morning and then not tell me what you’re up to.”

“Y/N, I need you to trust me, okay? I’ll tell you soon, I promise” he tried to reassure her, hoping she’d understand. “It’s something for us, for our future and I just want things to be perfect.”

“But do you really have to be away every Saturday? I mean, what the fuck am I supposed to think is going on, Dean? You’ve been busy during the week, the least you could do is spend some time with me on the weekend, but no! You keep leaving at the earliest possible hour and you come back late at night!” she said, glaring at him as her voice raised slightly. She got up quickly, the chair scraping harshly against the floors.

“You’re not supposed to think anything, Y/N” he snapped. “You’re supposed to trust me, that’s it.”

“Well, it’s kind of hard to do that when you’re never here” she scoffed as she walked away from the table and into the kitchen. Dean shook his head, following behind her.

“I’m not the only one who hasn’t been here” he threw back at her.

She laughed bitterly, and Dean felt his stomach turn at the sound.

“Really? Then what is all of this?” she asked, gesturing to the food on the stove. “I’m here every day, making sure you have what you need when you get back at god knows what time of night!”

“That maybe so, sweetheart… but that” he said, gesturing to the table with the tests on it. “That’s when you’re not here! I try to talk to you and you’re always so lost in what you’re doing, you can’t even hear me!” Dean yelled.

“Fine, then let me make it easier for you” she hissed, as she walked to the table and gathered up all the tests. She shoved them into her handbag, picked up her coat and put it on over her oversized sweater, to keep her exposed legs warm.

“Y/N stop” Dean said, shaking his head. “Please, stop.”

That was not going well at all and he felt horrible for even bothering her while she had been working. She was working. It’s not like she was ignoring him on purpose.

“For the record, this is my job” she snapped at him as she turned around. “And you holding it against me is something I’m not going to stand for.”

“Y/N, wait-” he started but she walked out the door so quickly, slamming the door behind her, he barely had time to register it.

He had the first thought of following her, but the second thought of knowing she needed space, stopped him. That was the first time they had fought, and it was bad. He had blamed her work for the reason she was distant, but it was the fact that he was keeping something from her that caused her to be so upset. Plus, all these days apart hadn’t helped them in their relationship.

He knew he had to fix this and soon. He just hoped he hadn’t royally screwed up.

That night after Y/N finally finished grading the tests, she angrily washed her face before putting on her pyjamas and getting into bed. She glared up at the ceiling of her bedroom, shaking her head. He was the one who was hiding something and then blaming her for being distant because of her work. She had to distract herself from thoughts and insecurities about what might be happening, with her work. He had some nerve to blame her for this.

Though… she hadn’t exactly helped by saying that he was never there. Yes, it was sort of true, but she knew how hard he was working at the new garage, while also trying to keep things up and running at the old one. She knew he loved his work so much and she never wanted him to think she would be angry at him because of it. She really hoped he wasn’t thinking that.

She knew she needed to sleep on it and figure it out the next day. She just hoped she could.

* * *

It had been a restless night for Dean. Not sleeping next to Y/N was definitely the biggest factor of that, but their fight had been playing on his mind all night too. He woke up to go to work and was yet to see her that day.

He hated that he brought her job into their argument. She was great at what she did, she was passionate, and she always supported him, so he had to support her too. He hated that for a minute back there he used it against her. He knew as soon as he got home, he had to speak to her. One night without her next him was enough to scare him. He never wanted to be without her, even for one night.

**Dean:** _I hated not having you next to me last night. I’m clocking out early today, we have to talk, sweetheart. I’m so sorry about what I said. I love you._

He had sent her a message during the day and he just hoped that she would want to actually talk to him when she got home. He was going to make it a point to be home before her, so that she knew he was serious about this. He needed her to know that.

He was glad that work was a good distraction at that point. It was the middle of the day, he had a few hours left of work, and he had to tow someone’s car back to the garage. Hopefully he could continue to distract himself for the next few hours, until he returned home and dealt with the aftermath of the night before.

As he drove back to the garage, he stopped at a light and thought about what he was going to say to Y/N when she got home. He was scared and didn’t know if he would just end up ruining everything more than he already had. He couldn’t lose her. Not now, not ever. He really had to think carefully about what to say.

As the light turned green, Dean moved the tow truck forward, ready to head back to the garage. However, he didn’t have time to react as another car ran a red light and hit the tow truck on the passenger side, sending it screeching along the road a few feet away.

The last thing on Dean’s mind as he blacked out was Y/N.

* * *

The night had not been restful for Y/N either.

She was embarrassed about how she had reacted. She shouldn’t have doubted Dean and what he was doing. She always said she would trust him and now she made him doubt whether she did or not. She did. She completely and unconditionally did, but she did have her fears about what he was doing. If he couldn’t tell her, then clearly something was wrong. Or maybe nothing was wrong, and she was just a bitch for overreacting.

She was glad when she got a message from him saying he’d be home early. She knew they needed to talk before things got worse.

**Y/N:** _Okay. I’m so sorry too. I do trust you, Dean. You have to know that I do. We’ll talk when I get home. I love you, so much._

She had spent nearly the whole day at work with this at the back of her mind. She was so distracted at work and everyone could tell that something was wrong. Some of the teachers had asked her if she was okay when she was in the staff room, but she just played it off like she didn’t get a lot of sleep. However, when Charlie asked when they went to the staff bathroom before their next classes, Y/N told her everything.

“I made a mess of everything, Charlie” she said, shaking her head as she leaned her hands on the sink.

Charlie shook her head, as she rubbed her hand up and down Y/N’s back. “No, you didn’t. Do you guys need to talk about it? Yes, of course, but you haven’t made a mess.”

“But I’ve made him doubt my trust in him. I don’t want him to think I don’t trust him” Y/N choked out, trying to keep her emotions at bay.

“No, you haven’t made him doubt anything, Y/N. He loves you, and he knows you love him, trust him. You just have to talk it out. He’s going to be the one to tell you everything, but all I’m going to say is that it’s a good thing; what he’s waiting to tell you. I promise” Charlie reassured her, smiling at her, softly.

“It’s going to make me feel even worse, isn’t it?” Y/N asked, frowning.

Charlie wasn’t going to say anything, but when Y/N lifted an eyebrow, she sighed. “Yeah.”

“Great” Y/N shook her head, closing her eyes.

“But it’s also going to make you feel really good, really excited, and that’s it. That’s all I’m going to say” Charlie said, trying not to smile as she thought about it.

“Okay” Y/N nodded.

The next class went on and on, as she taught the kids and distracted herself. She was incredibly glad when that bell rang at the end of the day and she could finally get home. She didn’t say her goodbyes to anyone, just picked up her bags and lunch that she couldn’t finish because she didn’t have the stomach for it and left the school.

As she drove home, she could feel her heart beating wildly as she thought about Dean coming home and what she was going to say to him. She had to fix this and promise him that she would never doubt him ever again. She loved him and she trusted him; she needed him to really know that.

As she drove, a soft melody started on the radio and she instantly knew what song it was.

_Is love so fragile_

_And the heart so hollow_

_Shatter with words_

_Impossible to follow_

_You’re saying I’m fragile I try not to be_

_I search only for something that I can’t see_

_I have my own life and I am stronger_

_Than you know_

_But I carry this feeling_

_When you walked into my house_

_That you won’t be walking out the door_

_Still I carry this feeling_

_When you walked into my house_

_That you won’t be walking out the door_

Y/N felt the tears in her eyes stream down her cheeks as she finally let out the emotions of what happened. All she could think about was how she did walk out the night before, and how she regretted it instantly but made no move to turn around and go back to him. How could she do that?

_Lovers forever face to face_

_My city your mountains_

_Stay with me stay_

_I need you to love me_

_I need you today_

_Give to me your leather_

_Take from me my lace_

The song hit too close to what she was feeling, and she flicked the button, turning the radio off. She was almost home, anyway.

She wiped her eyes as she turned down their street, speeding up to reach the house quicker. She parked in her driveway but frowned when she didn’t see the Impala parked at Dean’s. Maybe he was still on his way home.

Suddenly, her phone rang and she picked it up, frowning when she saw ‘Sam’ instead of ‘Dean’. She thought maybe he would call and tell her he was on his way, but as she picked up the phone, that thought was quickly replaced with worry when she heard Sam’s frantic voice.

“Y/N! Where are you right now?” he asked, his breath short as he sounded like he was rushing around, and he sounded scared.

“I just got home… Sam, what’s wrong?” she asked in return, feeling her throat constricting as fear gripped her heart.

“The hospital just called me, they said Dean’s been in an accident. I’m on my way but if you can get there before me-” he replied, but she cut him off as she turned her car back on.

“I’m leaving now!” she yelled as she hung up and pulled out of the driveway and drove down the road towards the hospital.

She tried not to let the worst possible thoughts enter her mind, but that was hard to do when it was one thought after another, constantly. She felt like she couldn’t breathe; like her throat was closed and she couldn’t even gasp for breath. She frantically pulled into an empty spot in the hospital parking, grabbed her bag and rushed towards the entrance. She went to the desk and tried to find her voice as the nurse behind the desk looked at her.

“I’m here to see Dean Winchester, he was brought in” she said through short breaths, as she tried to calm herself down.

“Are you his emergency contact?” the nurse asked, as she started clicking the mouse and typing something on the computer in front of her.

“N-no, I-I’m not, but his brother is on his way-” Y/N started but the nurse shook her head, sternly.

“I’m sorry, ma’am. I can’t tell you anything without Mr. Winchester’s next of kin here” she said, looking between Y/N and the screen.

“No, please, I have to know if he’s okay” Y/N shook her head, frantically, trying to reason with her. “Please, you have to tell me.”

“He’s with the doctors right now, but that’s all I can say. I’m sorry” the nurse said, giving her one bit of information she was allowed to give, which wasn’t very telling about Dean’s condition.

Y/N stepped back from the desk, letting out a sob she had been holding back as she drove over there. She cradled her head in her hands, letting the last several hours wash over her as she descended into silent tears, in the middle of the waiting area. Something could be seriously wrong, and she wasn’t allowed to know until Sam got there. She could lose Dean and the last thing that ever happened between them would’ve been that stupid fight. She felt the guilt settle in as she continued to cry quietly, trying to be positive but failing.

“Y/N!” she heard someone yell. She looked up and walked over to Sam as he rushed towards her, dressed in a suit. He had clearly rushed straight out from work.

“Sam!” she launched herself into him, hugging him tightly. “They won’t tell me anything, they said you had to be here.”

“Okay, it’s okay, come with me” Sam was being as calm as he could be, holding her hand in his as he walked over to the desk.

“I’m Sam, Dean Winchester’s brother” he told the nurse. “Please tell us what’s going on.”

“Dean was brought in after a car collided with his tow truck at an intersection. The doctors are with him but let me get an update for you” the nurse informed them and picked up the phone.

“Alright, thank you” Sam said, as he stepped away and sat down on a chair. Y/N sat next to him; their hands still clasped.

“Sam… what if he’s-” she started but stopped, unable to even say the words.

“He’s not” Sam shook his head, but he wasn’t sure whether it was out of conviction or denial. “He can’t be.”

“I fucked up, Sam” she whispered, as tears fell down her face.

He looked confused as he looked at her. “What do you mean?”

“W-we had a s-stupid fight yesterday, and I stormed out… and-and I-I slept at my house” she stuttered, not being able to say anything properly. “And now he… he’s here. If something happened-”

Sam turned to her, gripping her shoulders to make her look at him. “Nothing happened, Y/N. Dean’s going to be just fine, I feel it. And you didn’t fuck up. You and Dean will work it out. It’ll be okay, Y/N. I know it will” he reassured her, as he pulled her into a hug. She nodded against him, not trusting her voice anymore.

“Mr. Winchester” the nurse from before gestured to them, and they got up quickly.

“Yes?” Sam said, taking Y/N’s hand again. She felt like she was about throw up as she waited for the nurse to talk.

“Dean has a mild concussion, a cut on his forehead that the doctors sutured and bandaged. They’re going to keep him overnight for observation but he’s going to be okay” she explained, a soft smile on her face.

Y/N let out a harsh breath as she sobbed, hugging Sam tightly when he pulled her in.

“Can we see him?” Sam asked.

“Yes, he’s in room 302, 5th floor” she replied, checking the room and telling them.

“Thank you” Sam said, as Y/N picked up her bag from where she had been sitting and joined Sam at the elevator.

Y/N and Sam rode the elevator up to the floor and found the room, but Sam stood back as Y/N walked to the door. She frowned as he stood behind her, a small smile on his face.

“You should go in first” he said.

“Sam, he’s your brother-” she started but he stopped her as he placed a hand on her shoulder.

“I know how scared you were when they couldn’t tell you anything. You need this, Y/N” he smiled softly at her. “I’ll be in soon.”

“Okay. Thanks” she said, reaching up high on the toes of her shoes and kissing his cheek.

Y/N turned the door handle and opened the door, feeling like the wind was knocked out of her all over again. Dean was asleep on the hospital bed, looking small in the big, bare room sparse of any color. The monitors beeped at a normal pace as she walked in and stood near the bed. She took in his face, a white bandage on his forehead, some small cuts and scrapes on his cheeks and hands as her eyes travelled down his body. She felt tears roll down her cheeks as she sat down on the chair next to the bed. She curled her hand around his, sniffling as she watched him.

“Dean” she called out, softly. “It’s Y/N. I’m here.”

She saw his eyes moving under his lids, as he slowly started to blink them open, flinching at the stark light of the room. Dean’s head felt heavy as he looked around the room, his eyes finally landing on Y/N. She smiled at him through tears and he felt his heart soaring as he saw her there, in the room. She was there. He was there and he was alive.

“Y/N” he croaked, trying to smile at her.

“Shhh, don’t talk” she whispered as she took the plastic cup of water from his table and placed the straw to his mouth. “Here, slow sips.”

He took a few sips of water and gulped it down, looking at her as she put the cup down. He gripped her hand in his.

“You’re here” he whispered as he looked at her.

“Of course I am” she said, softly as she leaned down and kissed his hand. “Did you think… did you think I wouldn’t be?” she asked, scared of the answer.

“I… I would’ve deserved it” he said, coughing slightly. “For what I said to you-” he started but she gripped his hand, shaking her head.

“It’s okay, Dean” she whispered, not wanting to think about that anymore. It was stupid in comparison to what happened.

“No, I shouldn’t have brought your job into it, Y/N. I’m sorry” he said, groggily as he shook his head.

“I’m sorry, too. For doubting you… for thinking you were being dishonest about something” she apologized, kissing his hand again.

“I promise I’m going to tell you… I just… I wanted it to be a surprise. And… I promise I won’t ever say you’re never here. We’ve just been busy, but we’ll make time. And I promise I won’t ever bring your work into an argument” he said, shifting a little so he was sitting up a bit more. She tried to stop him, but he was adamant on being to look at her properly and apologize.

“I promise I won’t ever doubt you again, or be angry about you working late. I know you’re doing it for a reason” she said, gripping his hand tighter.

“Come here” he smiled softly, as he tugged on her hand. She smiled in return and got up, sitting on the bed next to him. She leaned over as he lifted his other hand, pulling her in for soft, slow kiss.

She sniffled as she pulled away, more tears rolling down her face. “I hate that the fight could’ve been the last thing you remembered of me. I could’ve lost you today. And… they wouldn’t tell me anything until Sam got here-”

“Damn” he mumbled, shaking his head. “We’ll fix that tomorrow.”

“I was so scared” she cried, as she leaned into him, her tears beginning to stain his hospital gown.

“Me too” he admitted, as he pulled her in tighter. “I saw you before it all went dark. I saw…” he trailed off, not being able to tell her as her sadness got to him, a few tears rolling down his cheeks, too.

“I love you” she choked out, as she looked at him. He leaned in, kissing her harder than before, their desperation to be close getting to them.

“I love you, too” he muttered against her lips as he kept kissing her. “And for the record… there’s plenty of things I’d remember about you before that fight.”

She smiled at him as she moved forward, kissing him again, not wanting to stop.

“Oh, sorry” they both turned to see Sam standing in the doorway, his timing way off as he walked in on the emotional moment.

“Hey, Sammy” Dean said, as he continued to hold Y/N close.

“Hey” Sam said, sighing in relief as he saw his older brother looking alright for the most part. “I’m glad you’re okay.”

“Yeah” Dean nodded, as he leaned his head against Y/N’s.

Sam and Y/N both stayed until visiting hours were over, as they weren’t allowed to stay overnight. She didn’t want to be apart from him for another night, but Dean told her it would be okay. Sam had already called Benny and told him what happened, telling him that Dean wouldn’t be at work tomorrow. Y/N had made the decision that she would take work off the next day and take care of Dean.

* * *

Y/N picked Dean up the next morning, filling out his discharge forms, adding her name and contact information to his contact list, before driving him home. For the rest of the day, it was like she was still at school as she told Dean to relax and to give it a day before he started doing things again. By the end of the day, he was so tired that he was out like a light as soon as his head hit the pillow.

The following day, he was feeling much better and went to work for light duties, as Y/N also went back to work. When they got home, they relaxed and had a simple dinner, just spending time together that they hadn’t gotten to do in the weeks before.

Before they knew it, Friday rolled around. Dean was a hundred precent by then, and ready to take Y/N out that night. She had insisted they stay home but he had insisted harder that he was absolutely fine and ready to take her out for a much-needed date night.

Dressed in a gold, satin, strappy top and a black leather skirt that came to just at her knees, Y/N put on her black coat and black heels as Dean greeted her at the door. He was wearing a deep red, V-neck sweater and looks so gorgeous that she couldn’t think about anything other than ripping it off him.

Dean drove them into the city, feeling surprisingly okay about driving after the accident. He told her that had things been much worse, maybe he wouldn’t have bounced back to driving so quickly. He drove through the streets, parking in one of the side streets. They had a quick dinner at one of their favorite spots before Dean payed and then took her to where he really wanted to. They walked down the street, clinging to each other as the chill of the air blew around them. Dean led the way to where he was taking her.

Y/N smiled as she saw that he had brought her to a jazz club, walking through the velvet curtain and being brought to their booth table. The band was already on fire, a blonde woman singing her lungs out with a husky, whiskey touched voice that was electric. The lights were dimmed, a candle on each table adding to the glow. Y/N sipped her wine as Dean sipped his whiskey.

“This place is great” she said, smiling at him as she swayed to the music.

“I thought you’d like it” he smirked. “Think of it as an apology.”

“No, you don’t have anything to apologize for, not anymore” she shook her head, cupping his face. “It’s in the past.”

“Okay” he nodded. He looked into her eyes, smiling brighter. “God, you’re so damn beautiful.”

She felt the heat rise in her cheeks at his complement. “Dean.”

“Don’t ‘Dean’ me, sweetheart. It’s true. I know how lucky I am to have you. Especially after what happened. It… it could’ve ended so differently” he grimaced, as he remembered the day of the accident.

“I know” she nodded, but then shook her head. “Let’s not think about it.”

“You’re right” he agreed, as he leaned over and kissed her, quickly deepening the kiss.

“Alright, this next one’s for all the lovers in the house” the woman on stage announced. “Feel free to join the floor.”

A sexy, slow beat of the piano and bass started, as Y/N watched a few couples get up and move in close to each other. Suddenly, Dean stood up and smirked at her, offering his hand.

“Dean, no” she laughed, shaking her head.

“Come on, sweetheart” he said, wiggling his fingers. She bit her lip and stood up, taking his hand in hers. Dean led them over to the floor, and pulled her in close, his arms around her waist, close to her behind. She wrapped her arms around his neck, smiling at him.

_Do I move you?_

_Are you willing?_

_Do I groove you?_

_Is it thrilling?_

_Do I soothe you?_

_Tell the truth now_

_Do I move you?_

_Are you loose now?_

_The answer better be_

_That pleases me_

Dean swayed him and Y/N side to side to the beat, looking into her eyes. He leaned his forehead against hers, pulling her in closer.

_Are you ready_

_For this action_

_Does it give you_

_Satisfaction_

_Are you hip to what I’m saying?_

_If you are now_

_Then let’s start swaying_

_The answer better be_

_That pleases me_

_When I touch ya_

_Do you quiver?_

_From your head_

_Right down to your liver_

Dean’s hand moved up her back, his fingers brushing against the exposed skin of her neck and shoulder blades, causing Y/N to shiver as she bit her lip and looked him in the eyes.

_If you like it_

_Let me know it_

_Don’t be psychic_

_Or you’ll blow it_

_The answer better be_

_That pleases me_

Dean leaned in, pressing his lips to hers in a searing kiss. She cupped his face, holding him there, before he pulled away and winked at her.

“Let’s get outta here” he whispered into her ear, taking her hand in his and quickly leading her out, after paying for their drinks.

* * *

Dean and Y/N burst through the door of Dean’s house, lips pressed against each other’s as they pushed and pulled at each other’s clothes. It had been far too long since they had been together in this way, and they couldn’t keep their hands off each other.

“Get this off” she whispered against his lips as she tugged at his sweater. Dean pulled it up and his arms through it, tossing it somewhere on the floor. He reached around her and unzipped her skirt, watching her push it down and strip her top off too, leaving her in a black strapless bra and matching panties, thigh-high stockings and garter belt holding them up.

Dean picked her up and she wrapped her legs around his waist as he carried her into the bedroom, dropping her gently on the bed. He smirked down at her as he breathed heavily, leaning down on top of her as he kissed her jaw, neck and travelled down her body. He kissed her breasts, licked a path down her torso and stomach, as he reached down and pulled her thong to one side, inserting two fingers into her already wet heat.

She moaned loudly, smiling as she felt the pads of his fingers rub along her walls. “Just like that, fuck. Dean.”

“I can’t wait to fuck you, sweetheart” he mumbled against her skin. “It’s been too fucking long.”

“I can’t wait, either” she gasped, as he thrust his fingers in and out of her, throwing her head back with a moan as he hit her g-spot with precision.

He moved his head down, his mouth finding her clit as his tongue swirled around the little bud. He moaned at the taste of her, not having done this in a while.

“Fuck, you taste so good, Y/N. Your pussy feels so great wrapped around my fingers” he groaned against her mound.

“Dean” she said, trying to reach for him impatiently. “Fuck me. Please.”

He chuckled as he moved away from her, looking down at her. “So desperate for my cock, huh?”

She whined frustratedly as she grabbed his hand gently and moved it away from her, his fingers covered in her slick. She sat up as he kneeled over her, unbuckling the belt and unzipping his dark wash jeans, pulling them down along with his boxers. She wrapped her hand around his cock, pumping it up and down along the hard shaft.

“Fuck” he grunted, feeling her hand against him. He leaned forward and kicked off his boots, taking off his jeans and boxers. Once he returned to the bed, he smirked as Y/N pushed him onto his back and climbed on top of him, straddling his hips. She held his hard cock to her entrance and sunk down on him, letting out a long, loud moan as she felt him completely seated inside her.

“Fuck yeah” he muttered as he held onto her hips and looked up at her, looking so damn beautiful in that moment. Her eyes closed as she adjusted to him, her hair flowing down, her mouth hanging open. “Ride me, sweetheart.”

She planted her hands on his chest, using him as leverage to move her hips up and down, feeling his cock against every ridge inside her as she set a moderate pace.

“Dean… fuck! You feel so good” she moaned, wantonly as she looked down at him. She rolled her hips back and forth, as his lifted up to meet hers. On each thrust down, she circled her hips, causing Dean to throw his head back, his neck straining, veins popping against his skin.

“Fuck yes! Do that again, sweetheart. You know how much I love it when you do that” he told her. It was his favorite move of hers, that drove him wild every time.

She smiled with a naughty wink, doing it again. “You like that, baby?”

“Yeah, fuck yeah. I love it so much, Y/N. Love it so much” he rambled, not being able to concentrate on anything but the feel of her.

She hummed as she bit her lip. “I love it, too. I love the way your cock feels inside me, fucking me so good, so deep. No one’s ever fucked me the way you do.”

Dean let out a strangled groan as she began to bounce on top of him, tossing her head back as she let out a string of loud moans.

“And no one else ever will, right sweetheart?” he asked, gripping her hips tighter, as her ass slapped against his thighs.

“No one, Dean. No one” she shook her head as she unclasped her bra, tossing it aside before grabbing her breasts and tweaking her nipples between her fingers.

“You’re mine, aren’t you, Y/N?” he smirked up at her. She looked down at him and nodded, frantically.

“Yeah, I’m yours” she replied, looking into his eyes. “Only yours. I love you. I love you, so much.”

“I love you, too” he said, taking her hands off her breasts and curling their fingers together. Her thrusts became faster, as she continued to grind against him. She was close and so was he.

“Dean, oh fuck, I’m gonna cum” she said, feeling the coil in her belly begin to tighten.

“Cum with me, Y/N. Fucking soak my cock” he growled, as he drove his hips up harder on the last few thrusts.

“Fuck! Oh fuck, Dean! I’m cumming!” she screamed, as her body shook and the coil snapped, her eyes closing tightly. Wave after wave of pleasure washed over her and didn’t seem to stop at all as her juices flowed out of her and over his cock.

“Shit, Y/N! Oh fuck, yes!” he shouted into the privacy of the room, his cum shooting into her as his own climax hit.

Y/N breathed heavily as she rolled off him, landing on her back on the mattress. She moved her hands up and down her body, feeling it wet with her own sweat. Her hand moved down to her pussy, smiling as she felt his cum dripping out of her. She closed her legs, wanting to leave it there within her as she looked over at him, seeing him smirking at her.

“That was fucking incredible” he huffed, trying to catch his breath.

She nodded, feeling her eyelids grow heavy. He saw her and smiled, standing up on shaky legs and walking into the bathroom.

Dean came back with a wet washcloth and sat down next to Y/N. He parted her legs, swiping the cloth against her folds, the warm water cleaning her up. She looked up at him with a smile as her eyes continued to open and close. He cleaned himself as well and tossed the cloth in the hamper of dirty clothes, before returning. He smiled softly as he saw that she had fallen asleep, as he moved the covers over her and got in next to her, pulling her close.

Y/N looked up at Dean, smiling softly as she leaned in, pressing her lips to his. She looked at him, taking in his green eyes, sharp nose and freckles scattered across it and his cheeks.

“You okay?” he asked, softly.

“Yeah” she replied, nodding. “Just thinking.”

“About?” he wondered; his voice gravelly as he lowered it.

“About… the accident” she said, feeling tears prick at her eyes. “I…”

She shook her head, burying her face in his neck, her body shaking as she began to cry. Dean held her close, whispering soft words to her.

“Sweetheart, I’m okay. I’m here, and I’m not going anywhere” he told her, reassuring her that everything was fine. He knew she had been keeping a brave face after the hospital, and she finally let it all out.

“I don’t want to be without you” she sobbed. “What would I do without you?”

“You won’t ever find out, Y/N. I swear it” he promised, cupping her face and making her look at him. “I’m not leaving you. Not now. Not ever.”

She nodded as she wiped her eyes, feeling emotionally exhausted. She leaned her head against his shoulder, breathing deeply as she tried to calm herself down. As her breathing slowed, she closed her eyes, letting sleep take over her.

Dean closed his eyes only once he knew she was safe and asleep, sleep quickly finding him, too.

* * *

Light filtered through the window into the room, hitting the face of the woman sleeping, wrapped in the sheets. Y/N sighed softly, her eyelids blinking. She slowly opened them, smiling as she felt the warmth of the sun against her face. She frowned however, when the space next to her on the bed was empty, the sheets cold. As she sat up and held the sheet against her body, the smell of fresh coffee and bacon hit her nose, making her stomach growl from hunger.

Y/N dropped the sheet and picked up Dean’s t-shirt from the chair, slipping it over her body, covering her up to above her knees as it hung off her body. She walked out of the bedroom and down the hallway, the floors warm as Dean must’ve turned the thermostat up. She smiled as she saw him standing at the stove, in only his boxers as he flipped the bacon. His hair was sticking up in different directions and he looked absolutely adorable. She walked over and came up behind him, wrapping her arms around his torso as she leaned in, pressing her lips against his spine between his shoulder blades.

“Morning” she said, kissing him in that spot.

“Morning” he smirked, as he pulled her to stand in front of him. He leaned in, kissing her softly. “So… I have some plans for us today, if you’re not busy.”

“I’m free as a bird” she said, smiling up at him.

“Great” he smirked, as he took the bacon off the pan. “I’m taking you to see my secret Saturday mission.”

She looked up at him, a little shocked. “Really?”

“Yep” he said, popping the ‘p’. “It’s about time I told you what it was.”

“Okay” she said, a little nervous to know what it was.

“Hey” he said, getting her attention as he could see she was worrying. “I promise it’s a good thing.”

“I know, I just… you don’t have to just because I was worried. I’m not anymore, seriously” she rambled, but he stopped her by pecking her lips.

“I’m not, Y/N. I really want you to see what’s going on” he confirmed, smiling at her.

“Okay” she nodded, more excited this time.

“Good” he smirked. “Now let’s eat.”

After breakfast, Dean took her in the shower as he simply couldn’t resist her, and then they both got dressed. Y/N got dressed into a long sweater dress that had a split on the side, putting her long, black coat on over the top. They rugged up with their scarves, as Dean locked up the house. They got into the car and Dean drove through the streets of Lawrence, excited to finally show Y/N what he had been waiting to. He couldn’t wait to see her face when she saw what it was. Dean turned onto the street, moving forward down the road and cutting the engine as he stopped outside the house. Y/N looked around the street, a slight frown on her face.

“Where are we?” she asked.

“Well,” Dean started as he pointed up at the two-storey house, with a garden that was still yet to be made and a large porch. “That’s the Saturday secret.”

She looked up at the house, blinking a few times. “Meaning?”

“Meaning… it’s mine” he replied, with a small smile. “I’ve been renovating it for a few months. There’s still a lot of work to do, but it’s coming together.”

“That’s amazing!” she smiled, as she moved forward on the seat and hugged him. “You could’ve just told me.” She laughed as she pulled away, but frowned as she saw him looking at her with an expression she couldn’t quite place.

“I couldn’t because…” he trailed off, taking a deep breath. “Because it’s mine but… I want it to be ours. When we’re ready to move, I want us to move in here. Together.”

Her eyes widened as she was completely shocked. “But… but Dean it’s yours. If something happened-” He cut her off with a small chuckle.

“It’s ours. I’m going to call the office and get you added to the contract” he told her, smirking.

She smiled, feeling tears brimming her eyes. “Dean, that’s so sweet but… we’re not married. Anything could happen-” he cut her off again by shaking his head.

“Do you think something bad is gonna happen?” he asked, really wanting to know.

She thought about it for a second. She had no real reason to think that way, it was just a precaution they needed to take, wasn’t it?  
“Well, no… but it would be messy to change things to add me, wouldn’t it?” she wondered, shrugging.

“It’s nothing we can’t figure out, sweetheart” he said, simply. “And yeah, we’re not married but… we can get married. Some day.”

She stared at him, feeling faint. “Really?”

“Yeah” he nodded, not missing a beat. “It’s all on the table, sweetheart. Kids were already there, right?”

She nodded slowly as she looked at him, not trusting her voice.

“Then so is marriage” he said, taking her hand in his. “So… you wanna move in with me when it’s done?”

She laughed as she nodded, excitedly. “Yes!” she launched herself at him, hugging him tightly. He laughed as he buried his face in her neck, placing a small kiss there. He pulled away, smiling at her.

“Alright, let’s go in and I can show you what we’ve done so far” he said, tugging her hand to move out of the car.

“Wait” she stopped him. “I don’t want to see it.”

He frowned, not understanding her. “Why?”

“Because,” she started, smiling at him as a tear rolled down her cheek. “You wanted this to be a surprise for me. And I want that to still happen. No one… no one’s ever done anything like this for me. Everything you’ve done for me… it completely floors me, to this day. I like it when you surprise me because you keep doing that… so I don’t want to see it. Not yet.”

He smiled at her, nodding as he understood. “Okay. You still gotta help me though. I need to know what to do on the inside and I want your inspiration. Maybe you can use your home magazines that you keep, and you think I don’t know about.”

She looked sheepish, as she nodded. “Sounds good.”

He leaned in, kissing her passionately. She pulled away, leaning her forehead against his.

“I’m sorry I ever doubted you” she apologized. Seeing what he had been keeping from her made her feel so guilty, and she knew she needed to apologize again.

He shook his head, kissing her hand. “There’s no need for that, sweetheart. We’re good.”

Once they left, they drove into town. They felt like walking around, so they went to a few bookstores and record stores, picking up a couple that they liked or didn’t have yet. After, they had some lunch at one of their favorite diners before they came back home.

Y/N was so relieved that everything was out in the open, and nothing was as bad as what she had been thinking. In fact, it was all amazing. The house was incredible, and she couldn’t wait to see what Dean would do with it. She smiled as she walked into his house, thinking about their conversation in the car.

He had put marriage on the table. It probably always was considering kids were on the table, but this was the first time he’d said it out loud. In a flash of his words, she imagined herself as his wife, her heart beating wildly at that thought. She knew that he was the only person she could ever attach herself to in that way, and she was glad to know that he was thinking about it, too.

Dean smiled as she watched Y/N going about his house, making herself a cup of tea in the kitchen. He could so easily picture her in the new house, once it was done, the images of his dream returning to him. He couldn’t wait to spend his whole life with her. When he was younger, thinking on those terms was downright terrifying, but not anymore. Not when you have someone who loves you unconditionally and wants to spend every day making sure you’re cared for. That’s how she made him feel.

Later that night, they cooked dinner together. Dean’s lasanga that she loved so much that he made when she first came to his house for dinner. This time was much different, however. Now, she was helping him in the kitchen, playfully handing him things, as he stole kisses from her every now and then. One thing remained the same, however, both of them grooving to Zeppelin as they cooked.

_Leaves are falling all around_

_It’s time I was on my way_

_Thanks to you I’m much obliged_

_For such a pleasant stay_

_But now it’s time for me to go_

_The autumn moon lights my way_

_For now I smell the rain_

_And with it pain_

_And it’s headed my way_

_Ah, sometimes I grow so tired_

_But I know I’ve got one thing I got to do_

_Ramble on_

_And now’s the time, the time is now_

_To sing my song_

_I’m goin’ round the world, I got to find my girl_

_On my way_

_I’ve been this way ten years to the day_

_Ramble on_

_Gotta find the queen of all my dreams_

Dean stirred the sauce in the pot, reflecting on the words of one of his favorite songs. He had spent years, flirting and sleeping around with women. Years of rambling on, trying to find somewhere to settle, maybe even someone if he was lucky enough to ever find the one for him. He thought he had found a good thing until it went sour incredibly quickly.

Then Y/N came into his life. Shining like a beacon from across the street; something he immediately gravitated to. It became apparent to him very soon, that she was it. She was the one. The woman he had been looking for all his life, without really seeking her out.

She was the queen of all his dreams.

Dean walked up behind her as she chopped up some basil, kissing her head. She turned around, wrapping her arms around him and kissing him, softly. She looked up at him, her eyes gazing into his with the most loving expression. One he had seen several times now, but it suddenly felt like she was seeing him for the first time.

“What is it?” she asked, knowing he was thinking about something.

“I get it” he replied, knowing it wasn’t clear but also knowing she’d ask him again.

“Get what?” she asked, confused.

“Why you’re the one” he replied, not missing a beat. No pause. No hesitation. He leaned in, kissing her passionately.

Y/N smiled into the kiss as Dean pulled her in closer, resting her forehead against his. She knew he was the one for her too. After all the years of heartache and pain, years of wondering if she’d ever be good enough for someone, she finally found the man who would do absolutely anything to make her happy. She finally found the one she was always meant to be with.

They had learned a lot along the way, had spent months trying to fight their feelings for each other, before they finally realized they couldn’t deny it any longer.

They gazed into each other’s eyes, seeing nothing but love as they quietly acknowledged that moment as the start of something new.

Something new that they couldn’t wait to explore.

Together.

**Notes for the Chapter:**

> The last chapter! Epilogue is next! I really hope everyone has enjoyed this series! :)


	16. Epilogue: A Lesson in Making a Life

**Summary for the Chapter:**

> A snapshot of Dean and Y/N's relationship over 6 months.

**Notes for the Chapter:**

> SO MUCH FLUFF, YOU GUYS. Some swearing, Lots of kissing, Happy Tears, Dean being the cutest and sweetest he’s ever been in this series. Implied sex. Just a whole bunch of happiness. I don’t want to say anything and ruin the surprise, but there’s absolutely nothing but fluff here!

* * *

**6 MONTHS LATER**

_If the sun refuses to shine_

_I would still be loving you_

“So, you don’t know what he has planned for tonight?”

Y/N stood in front of her mirror, applying her make-up. Charlie, who sat on the bed behind her, had just asked her that question, to which Y/N shook her head.

“No idea” she said, before picking up her eyeliner and bringing it to her right eye first.

Meg walked into the room, handing Charlie one of the glasses of water she had in her hands. “If he told you to dress up, it’s something important.”

Y/N smiled, shrugging her shoulders. “Maybe. I just want to have a good time tonight. He’s been so busy with the house; we can finally relax tonight.”

“You still want it to be a surprise, huh?” Charlie asked, smiling.

“Yeah” Y/N replied, quietly, smiling to herself.

A lot had happened in Dean and Y/N’s life.

They had spent nearly every waking moment together, when they weren’t at work or with their friends or Dean’s family. To say that they fell more in love with each other every day was an understatement. They both couldn’t believe how much more they were able to give with each passing moment. Since Dean had told her about the house, they had begun planning everything for it together. She would give him her ideas from her home magazines, telling him different ways to go about doing the internal re-model. However, Dean being Dean, didn’t tell her which of her ideas he was taking on board. He had taken her saying she wanted to be surprised very seriously.

Y/N couldn’t believe how far they had come; from just being neighbors and liking each other, to a proper couple in the span of several months. She had met his family, and everyone loved her instantly. They had their first Valentine’s Day and Dean had pulled out all the stops, taking her to a fancy restaurant and then a hotel in the city for the night, taking work off the next day which she did too, enjoying spending time together before their late check-out.

Then, the time came for Dean to meet her parents. She had been nervous, but she knew her family would give him the same treatment that his gave her. They had come down from New York to visit her just as summer break started. Her parents along with her sister and brother-in-law and the kids all hauled themselves down to Kansas to see her and meet Dean. When she had told him, he had been incredibly nervous to meet them, but had agreed, nonetheless.

They spent an entire afternoon together, Dean played with Y/N’s nieces who were obsessed with him now, took her dad and Brian out for a spin in the Impala, and charmed her mom and Jill all day until her sister and brother-in-law returned to the hotel with the kids, as Y/N’s parents were staying with her. Dean had passed with flying colors, which they were both so relieved about. The family’s trip there pretty much cemented that things were serious, and they were moving onto a bright future together.

Once the family had left after visiting for a week, Dean took Y/N on a trip to California, on a two-week getaway that he cited they needed to take after working so hard for the last several months. It was their first trip together, and Dean had driven them down there. The beach house they got to stay in belonged to a friend of Sam’s from college, which they had all to themselves as the friend and his wife had gone to Europe for the summer. Sam and Eileen weren’t able to go, as she didn’t want to endure a long drive while pregnant, and she also couldn’t fly now. So, Dean took the opportunity to be alone with Y/N, spending a romantic trip away together. They spent their days on the beach, exploring the town and soaking up the sun, with their nights spent at bars, restaurants and night walks along the shore, before exploring each other once they got back to the house.

It had been exactly what they needed, both of them falling even more in love with each other if that was even possible.

Sam and Eileen’s son was born a week after the trip, both parents exhausted but over the moon with their bundle of joy. Dean and Y/N had taken on babysitting duties a couple of months later, knowing the parents definitely needed a break. As if seeing Dean with her nieces hadn’t been enough, Dean with his baby nephew was a sight to behold and had given Y/N plenty of thoughts she shouldn’t have had. Not for a while, at least.

She knew they were heading in that direction, and she also knew that Dean felt the same way, but it was better to not get carried away with thoughts of marriage and children until those things were properly on the cards for them.

_When mountains crumble to the sea_

_There will still be you and me_

Six months later, nearly a year to the day she had met him, and she had fallen harder with each day that passed. He made her feel loved, protected and safe. He cared about her and her job, her passions and her wants and needs. He was completely satisfying in every department, especially the bedroom, getting her to admit to fantasies she had hidden and even playing out a very particular one. She had given him his teacher fantasy, so it was only right he gave her one of hers.

Through it all, there was only one thought she had. That she wanted to spend the rest of her life with Dean Winchester. She wanted to make a life with him and only him. He was her person.

As Y/N reflected on everything that had happened, she quickly changed into her wine-red dress and nude heels, put on her thin, diamond, drop earrings and made sure her Y/H/C hair was still perfectly styled and her make-up was flawless, having gone for a lighter look with a light pink lip.

“So… how do I look?” she asked, turning to her friends.

“Beautiful” they both sighed, smiling at her.

“He’s not going to know what hit him” Meg said with a wink.

Just then, the doorbell rang a couple of times, signalling Dean had walked over to her house to come and get her. She still only used it to keep her clothes and do her work in her office, spending most of the days and all her nights over at Dean’s.

“Alright, I better go” she said, doing one last check in the mirror. “You girls stay as long as you want, just-”

“Lock up when we leave, we know” Charlie smiled. “Go.”

Y/N smiled as she walked out of the bedroom, Charlie and Meg hanging around in the hallway as they watched her greet Dean with a kiss.

“She really has no idea what’s going to happen soon” Charlie quietly squealed.

“I know” Meg said, excitedly as they both waved at Dean, giving him a thumbs up as he winked at them when Y/N’s back was turned. She smiled back at them one last time before shutting the door, leaving the girls in the house.

“I always knew they’d get to this point” Charlie said, beaming. “Gosh, I’m so happy she came into his life.”

“Amen to that” Meg said, as she clinked her glass of water against Charlie’s. They both took a few sips, before rinsing the glasses and picking up their bags.

“Alright, what time did Dean say they’ll be done?” Meg asked, as they stepped out the door and locked up Y/N’s house.

“Around 9” Charlie replied, as they got into her car.

“Good. That means we have enough time” Meg said, as she buckled her seatbelt.

They both couldn’t wait to help Dean make this a night Y/N would remember forever.

* * *

_Kind woman, I give you my all_

_Kind woman, nothing more_

Dean smiled at the look on Y/N’s face as the waitress popped the champagne he had ordered, pouring them each some in the champagne flutes before putting the bottle in the ice bucket, and walking away. He loved the look of surprise and giddiness on her face, but she really had no idea what was in store for her tonight.

“This is all too much, Dean” she said, shaking her head even though she was smiling. “Champagne, the restaurant to ourselves…”

He waved her off, smirking. “I’ve been coming here for years, so Tony owed me at this point.”

He had taken her to the restaurant he took her to on their first date, just six months ago. He had known the owner for years, coming in here often enough plus Dean fixing Tony’s car several times in the past few years, plus the place practically being an institution of Lawrence, all added up to Dean being able to have the place for themselves that night.

“Well, I’m glad it didn’t cost you much” she smiled, as she picked up her glass and held it up for a toast. “To six, amazing, official months, but to one whole year of knowing you.”

“To knowing you, too” he smirked as he clinked his glass with hers, secretly touched that she had said that.

Dean knew that he was truly blessed to have the amazing woman sitting in front of him, in his life. She had saved him from a life of misery, something he never would’ve realized or gotten out of if she hadn’t shown up and completely turned his life around, for the better. She made him feel appreciated, valued, cared for and loved. She was genuinely excited about his achievements when it came to work, and even gave him ideas on how to do things when he voiced that he was lost sometimes. She supported him and his passion, being equally passionate and driven, just in her own profession.

She was absolutely stunning, knocking him down a few pegs every time he looked at her, and god damn it, if she wasn’t the sexiest woman he had ever been with. She had fulfilled a fantasy of his, and he had returned the favor recently, finding out while he enjoyed her being dominant towards him, he absolutely loved seeing her being submissive for him.

He knew from the moment they met that she was going to be sticking around for a while. Then, a while turned into him wanting her around forever, once things became more serious between them.

Meeting her family sealed the deal for him, however. He wanted Y/N in his life for as long as they lived.

_Little drops of rain whisper of the pain_

_Tears of love lost in the days gone by_

They ate and drank, chatting about everything they could, enjoying each other’s company. They never ran out of things to talk about, and they both hoped they never would. Once Dean paid for dinner and dessert which had consisted of an incredibly rich chocolate cake, they took a stroll through the park to get to the car. It was a pleasant night, not blazing hot like it had been during the day, with a light, cool breeze. Y/N kept looking over at Dean, dressed in his best dark jeans, a light blue shirt and his good boots, proving that he always looked incredible.

Their hands were intertwined as they walked, stealing kisses and touches from each other as they made their way to the car. They could barely ever keep their hands off each other, but Dean was being extra lovey and Y/N had begun to wonder what he was up to.

“Ready for the next thing?” he asked, as he sat in the car, turning the ignition on.

“Absolutely” she replied, smiling brightly.

“Good” he said, before he reached over and opened the glove compartment, taking out a tie he had stashed in there. “Turn around, sweetheart.”

“Oh my god, Dean, what kind of thing do you planned?” she asked, her eyes widening as she saw the tie.

“It’s nothing like that, Y/N” he replied, as he nudged her to turn. “Unless you want it to be” he smirked, even though she had turned and couldn’t see him.

He wrapped the tie around her head, covering her eyes before tying it at the back.

“Is this really necessary?” she asked, pouting her lips.

He chuckled, leaning in and kissing them. “Yes.”

He pulled out his phone and sent a quick message before he started the Impala. The engine roared to life, before he put it in drive and made his way down the road.

* * *

They hadn’t been driving long, but Dean had taken several turns in the last few minutes. Y/N was confused as to where they were going but didn’t say anything. She knew he had a knack for surprising her, and she didn’t want to spoil that for him.

Dean quickly pulled up outside his newly renovated, two-storey house. He shut off the engine, just as he saw two figures walk out of the house. He got out of the car and smiled at Charlie and Meg who waved at him, before quietly making their way down the driveway and towards Charlie’s car. He waited until they had completely driven away before walking around the front of the car and opening the passenger door.

“Can I take this off now? What took you so long to get here from the other side?” she asked, starting to get a little suspicious now.

“Y/N, you gotta relax” he laughed, as he turned her around and held onto her shoulders, guiding her up the sidewalk, after he had locked the car.

He walked her up the path in the still-to-be-finished garden, which she wouldn’t be seeing at that moment. He carefully led her up the porch stairs, making sure she didn’t trip with her heels on. He opened the door and led her in, her heels echoing on the hardwood floors.

“Dean, what’s going on?” she asked, impatiently as she heard her shoes on the floors.

“Just one more second” he replied, as he moved in front of her and guided her through the hallway, past the living area and into the middle room. When he stopped, he felt his heart beating wildly in his chest.

“Okay… ready?” he asked, holding onto the tie being used to blindfold her.

“Yes” she replied, somewhere between exasperated and excited.

Dean laughed to himself, as he moved in front of her. “Okay. 1… 2… 3…”

He counted down and opened the knot, dropping the blindfold. He watched her eyes flutter open, smirking as they immediately widened when she realized where she was. She let out a loud gasp, her eyes flitting to every part of the room, lit up with candles everywhere.

Y/N couldn’t believe her eyes as she looked around the room, turning in circles to see every part of it. The hardwood floors, the beautiful dining table that she loved from one of her magazines, a large archway leading to the living area, still to be furnished. However, the thing that got her immediately was the huge kitchen. It was her dream kitchen, with a big island bench in the middle, a beautiful stove and oven, the cabinets painted a dark shade of green with gold handles, and marble countertops. There was a picture window in the kitchen with a ledge, with an empty glass box for her herbs.

Y/N looked back at Dean, his smirk wide as he bit his lip, gaging her reaction. She laughed as she launched herself into him, wrapping her arms around his neck. She felt tears prick her eyes as she shook her head.

“You like?” he asked, rubbing his hand down her back.

She pulled away slightly to look up at him. “Like?” She shook her head, as she looked around again. “Dean… I’m speechless. I-I… I absolutely love it.”

“Okay, good, because it’s still not quite done. I left a few things like the living area and painting unfinished, so they we can decide that stuff together.”

“It’s all perfect, and it’s going to be even more perfect once it’s completely done. Dean… it’s beautiful. It’s… it’s my dream house” she choked up, not being able to talk.

There were large windows in the living area, and large French doors that led out to the covered porch, and then the backyard.

“Everything’s done, just needs furnishing and your touch. Master suite is done but not furnished. Guest room’s done and we can put your bed in there for now, but I left the other two rooms unfurnished too… for… well, you know” he muttered, his cheeks turning red. He was already thinking about how their future kids.

She smiled through tears, leaning in and kissing him, feverishly. “I love you. I love that you put everything into this for yourself, for me… for our future family.”

_My love is strong_

_With you there is no wrong_

_Together we shall go until we die, my, my, my_

He leaned in and kissed her again, wrapping his arms around her waist as he pulled her deeper into the kiss.

“That’s a lot of candles” she laughed when she pulled away.

“Thank Charlie and Meg for that. They wanted to help make tonight special for you” he told her, smiling as he kissed her softly again.

“For us” she playfully corrected him.

He chuckled, nodding. “Yeah. Us.”

He looked down at her and Y/N smiled at him, squinting slightly as she noticed something different in his eyes. She couldn’t quite place it but it didn’t seem like it was a bad thing.

_An inspiration is what you are to me_

_Inspiration, look, see_

Y/N slowly pulled away from him and smiled as she walked away, going into the kitchen. She ran her hand over the countertops, opening cabinets and drawers, smiling the entire time. Dean was glad she had taken a moment to do that, as he took a deep breath, nervously touching his back pocket to his jeans. He smiled as he watched her; the dream he had so many times over the years was finally taking shape. She looked up at him and frowned, seeing his nervous stance as he stood there in the room. She walked over to him, placing her hands on his chest. He gulped as he looked down at her, a small smile tugging at his lips.

“Dean… are you okay?” she asked, her voice slightly scared.

“I’m okay” he nodded, as he took her left hand in his and brought it to his lips, kissing it. “In fact, I’m better than okay. I’ve been better than okay since you came into my life.”

She smiled at him, feeling the same way for him.

_And so today, my world, it smiles_

_Your hand in mine, we walk the miles_

“You came here and changed everything; you turned everything upside down in the best way possible, sweetheart. You made me realize what I was missing. You’ve been everything I’ve ever needed in my life. You’ve supported me and actually cared about what I do. I don’t know what I did to deserve you, but I’m so glad I have you. You saved me” he told her, pulling her in close as he looked into her eyes.

“Dean” she sighed, looking up at him with all the love she had for him.

“I want us to make a life here. I want us to be a family. I promise you, right here, right now – I’ll always take care of you. I’ll never hurt you, or make you feel you’re less than what you are. You’re beautiful, strong, smart, kind and caring. You love everyone around you, and they know that you’ve got their back. I know you’ve been hurt in the past, but I promise… I’ll _never_ do that to you. I never thought I’d get to have this; a beautiful woman to make a life with, but I know I don’t want it with anyone else but you” he said, as he moved back slightly.

Y/N’s eyes widened as Dean crouched down, getting down on one knee, her hand still in his.

_And thanks to you it will be done_

_For you to me are the only one_

“Dean” she gasped, as fresh tears welled in her eyes.

“I want you for the rest of my life, sweetheart. I love you, more than I ever thought possible to love someone. I promise I’ll love you for the rest of our lives” he smiled, his voice shaking with emotion. He reached into his back pocket and took out the little black box, opening it to reveal a beautiful, sparkling modest diamond ring in a platinum setting.

Y/N sobbed as she cupped her other hand over her mouth, the tears running down her face. She looked Dean in the eyes as he spoke, seeing everything he promised her, right there in his beautiful green orbs.

“Y/N Y/L/N… will you marry me?” he asked, his heart feeling like it would explode any minute.

Y/N pulled her hand away from her mouth, laughing through tears. “Yes! Yes, Dean, yes!”

Dean beamed, his smile brighter than ever before, as he took out the ring from the box and slowly slipped it onto her ring finger. He stood up, slightly off balance as she jumped on him, wrapping her arms around his neck. His automatically went around her waist, lifting her up, her heeled feet dangling above the ground. She pressed her lips to his, kissing him hard and passionately.

“I love you” she said, between kisses. “I love you, so much.”

“I love you too, sweetheart” he whispered, unable to stop kissing her. “Fuck, I love you so damn much.”

_Happiness, no more be sad_

_Happiness – I’m glad_

Y/N pulled away to look into Dean’s eyes, her face level with his. She leaned her forehead against his, tears still running down her face. Dean leaned in and kissed them away, smiling at her. She looked down at her ring, her smile beaming as bright as the diamond.

“It’s so beautiful” she said, wiggling her finger against the light of the candles in the room.

“It’s was my mom’s” he told her, smirking. “When I told her that I was planning on proposing, she gave it to me.”

Y/N was shocked as she shook her head. “She wanted you to give this to me?”

“Yeah, Y/N. She loves you; we all do. You’re a part of our family. She wanted you to have it… I want you to have it” he explained, looking into her eyes with all the sincerity of the situation.

“But, Eileen…” Y/N shook her head, not understanding.

“Sam bought his own ring back then, because he told mom when she offered hers that I should be the one to give it to someone. Who knew it would take this long to find the one woman worthy of it, but here we are” he said, smiling down at her.

Y/N choked out a sob, as fresh tears started. “I love it. I love you, Dean. I’m so happy.”

“Me too” he said, feeling his eyes getting misty.

They stood there in each other’s embrace, in the middle of the room, unable to stop kissing and touching each other. They weren’t sure how much time had passed. All they cared about in that moment was each other. However, Dean slowly put her down on her feet and took her hand, leading her across the room and up the wood staircase. He walked her slowly down the hallway once she admired the space near the landing, knowing that it would make a nice space for their future children. He led her past the rooms and into what would be their bedroom, smirking as he saw a few candles there too, blankets on the carpeted floor and a few throw pillows.

Dean turned to Y/N and pulled her close to him, leaning down and kissing her, feverishly. They slowly undressed each other as Dean laid her down on the blankets, her head on one of the pillows. Dean moved within her, wrapped tightly in her embrace, as they made love in their new home for the first time.

As they laid back against the pillows and basked in the afterglow, Dean leaned in and kissed her again, smiling against her lips as they continued their passionate exchange.

It wasn’t the first, and it certainly wouldn’t be the last.

There would be many more for years to come, as it held the promise of a lifetime together.

_If the sun refused to shine_

_I would still be loving you_

_When mountains crumble to the sea_

_There will still be you and me_

**Notes for the Chapter:**

> Thank you so much for reading! I really hope everyone enjoyed this. There's plenty more to come in the form of time stamps, and a possible sequel series! :)

**Author's Note:**

> What did you guys think? Please leave kudos or comment, I'd love to hear your thoughts! :)


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